(S)-(+)-3-Hydroxybutyric acid ethyl ester
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|
| |
Name | (S)-(+)-3-Hydroxybutyric acid ethyl ester |
Synonyms |
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Name in Chemical Abstracts | Butanoic acid, 3-hydroxy-, ethyl ester, (3S)- |
CAS No | 56816-01-4 |
EINECS No | 260-393-1 |
Molecular formula | C6H12O3 |
Molecular mass | 132.16 |
SMILES code | CCOC(=O)C[C@@H](O)C |
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fermenting yeast
sucrose |
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|
; Side reactions |
1H-NMR
1H-NMR: (S)-(+)-3-Hydroxybutyric acid ethyl ester |
500 MHz, CDCl3 |
delta [ppm] | mult. | atoms | assignment |
1.23 | d | 3 H | 4-CH3 |
1.27 | t | 3 H | CH3 (ethyl ester) |
2.46 | m | 2 H | 2-H |
3.55 | s | 1 H | OH |
4.16 | q | 2 H | CH2 (ethyl ester) |
4.15-4.23 | m | 1 H | 3-H |
Synthesis of (S)-(+)-3-hydroxybutyric acid ethyl ester
Reaction type: |
stereoselective reduction |
Substance classes: |
ketone, alcohol, enzyme, natural product |
Techniques: |
stirring with KPG stirrer, stirring with magnetic stir bar, adding
dropwise with an addition funnel, extracting, evaporating with rotary
evaporator, filtering, distilling under reduced pressure, column
distillation, vacuum pump, heating with oil bath |
Degree of difficulty: |
Medium |
http://kriemhild.uft.uni-bremen.de/nop/en/instructions/pdf/4022_en.pdf
|
0.1 mol |
Acetoacetic acid ethyl ester |
Educts |
|
Amount |
Risk |
Safety |
Acetoacetic acid ethyl ester |
|
Xi |
|
13.0 g |
R 36/37/38-41
|
S 26-36
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Catalyst |
|
Amount |
Risk |
Safety |
Yeast |
|
100 g |
R
|
S
|
Solvents |
|
Amount |
Risk |
Safety |
Diethyl ether |
|
F+ |
|
Xn |
|
400 mL |
R 12-19-22-66-67
|
S 2-9-16-29-33
|
Water |
|
|
R
|
S
|
Others |
|
Amount |
Risk |
Safety |
Celite 545 |
|
40 g |
R
|
S
|
D-(+)-Saccharose |
|
163 g |
R
|
S
|
Ninhydrin |
|
Xn |
|
|
R 22-36/37/38
|
S 26-28-36
|
Solvents for analysis |
|
Amount |
Risk |
Safety |
n-Hexane |
|
|
R 11-38-48/20-51/53-62-65-67
|
S 2-9-16-29-33-36/37-61-62
|
Diethyl ether |
|
F+ |
|
Xn |
|
|
R 12-19-22-66-67
|
S 2-9-16-29-33 |
Operating scheme
0.1 mol |
Acetoacetic acid ethyl ester |
Products |
|
Amount |
Risk |
Safety |
(S)-(+)-3-Hydroxybutyric acid ethyl ester |
|
8.26 g |
R
|
S 24/25
|
Waste |
Disposal |
evaporated diethyl ether
|
solvents for rectification
|
filter residue
|
solid waste, free from mercury
|
distillation residues
|
organic solvents, halogen free
|
.1 mol |
Acetoacetic acid ethyl ester |
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three-necked flask 2000 mL |
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bubble counter |
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internal thermometer |
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KPG stirrer |
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heatable magnetic stirrer with magnetic stir bar |
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addition funnel with pressure balance |
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suction flask |
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suction filter |
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apparatus for continuous extraction of a liquid |
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separating funnel |
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rotary evaporator |
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Vigreux column 8 cm |
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distillation apparatus |
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vacuum pump |
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oil bath |
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|
0.1 mol |
Acetoacetic acid ethyl ester |
Atom economy |
|
101.6 |
% |
Yield |
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63 |
% |
Target product mass |
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8.26 |
g |
Sum of input masses |
|
600 |
g |
Mass efficiency |
|
14 |
mg/g |
Mass index |
|
73 |
g input / g product |
E factor |
|
72 |
g waste / g product |
Chromatogram
GC: crude product |
column | DB-1, L=28 m, d=0.32 mm, film=0.25 µm |
inlet | on column injection |
carrier gas | H2, 40 cm/s |
oven | 50°C (5 min), 10°C/min --> 240°C (40 min) |
detector | FID, 270°C |
integration | percent concentration calculated from relative peak area |
GC: pure product |
column | DB-1, L=28 m, d=0.32 mm, film=0.25 µm |
inlet | on column injection |
carrier gas | H2, 40 cm/s |
oven | 50°C (5 min), 10°C/min --> 240°C (40 min) |
detector | FID, 270°C |
integration | percent concentration calculated from relative peak area |
13C-NMR
13C-NMR: (S)-(+)-3-Hydroxybutyric acid ethyl ester |
125 MHz, CDCl3 |
delta [ppm] | assignment |
13.8 | CH3 (ethyl ester) |
22.3 | C4 |
42.8 | C2 |
60.3 | CH2 (ethyl ester) |
64.0 | C3 |
172.4 | C1 |
76.5-77.5 | CDCl3 |
IR
IR: (S)-(+)-3-Hydroxybutyric acid ethyl ester |
[Film, T%, cm-1] |
[cm-1] | assignment |
3437 | O-H valence |
2979, 2936 | C-H valence |
1735 | C=O valence, ester |
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