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Showing posts with label TEXAS. Show all posts
Showing posts with label TEXAS. Show all posts

Tuesday, 21 July 2015

(S)-(+)-3-Hydroxybutyric acid ethyl ester

(S)-(+)-3-Hydroxybutyric acid ethyl ester

383
Name(S)-(+)-3-Hydroxybutyric acid ethyl ester
Synonyms
Name in Chemical AbstractsButanoic acid, 3-hydroxy-, ethyl ester, (3S)-
CAS No56816-01-4
EINECS No260-393-1
Molecular formulaC6H12O3
Molecular mass132.16
SMILES codeCCOC(=O)C[C@@H](O)C

Acetoacetic acid ethyl ester
fermenting yeast
sucrose
reacts to

(S)-(+)-3-Hydroxybutyric acid ethyl ester ; Side reactions




1H-NMR

1H NMR
1H-NMR: (S)-(+)-3-Hydroxybutyric acid ethyl ester
500 MHz, CDCl3
delta [ppm]mult.atomsassignment
1.23d3 H4-CH3
1.27t3 HCH3 (ethyl ester)
2.46m2 H2-H
3.55s1 HOH
4.16q2 HCH2 (ethyl ester)
4.15-4.23m1 H3-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 Xi
13.0 g R 36/37/38-41 S 26-36
Catalyst
Amount Risk Safety
Yeast

100 g R S
Solvents
Amount Risk Safety
Diethyl ether
F+ F+ Xn 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 Xn

R 22-36/37/38 S 26-28-36
Solvents for analysis
Amount Risk Safety
n-Hexane
F F Xn Xn N N

R 11-38-48/20-51/53-62-65-67 S 2-9-16-29-33-36/37-61-62
Diethyl ether
F+ F+ Xn Xn

R 12-19-22-66-67 S 2-9-16-29-33

Operating scheme

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
three-necked flask 2000 mL three-necked flask 2000 mL
bubble counter bubble counter
internal thermometer internal thermometer
KPG stirrer KPG stirrer
heatable magnetic stirrer with magnetic stir bar heatable magnetic stirrer with magnetic stir bar
addition funnel with pressure balance addition funnel with pressure balance
suction flask suction flask
suction filter suction filter
apparatus for continuous extraction of a liquid apparatus for continuous extraction of a liquid
separating funnel separating funnel
rotary evaporator rotary evaporator
Vigreux column 8 cm Vigreux column 8 cm
distillation apparatus distillation apparatus
vacuum pump vacuum pump
oil bath oil bath




0.1 mol Acetoacetic acid ethyl ester
Atom economy
101.6 %
Yield
63 %
Target product mass
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

crude product chromatogram
GC: crude product
columnDB-1, L=28 m, d=0.32 mm, film=0.25 µm
inleton column injection
carrier gasH2, 40 cm/s
oven50°C (5 min), 10°C/min --> 240°C (40 min)
detectorFID, 270°C
integrationpercent concentration calculated from relative peak area

pure product chromatogram
GC: pure product
columnDB-1, L=28 m, d=0.32 mm, film=0.25 µm
inleton column injection
carrier gasH2, 40 cm/s
oven50°C (5 min), 10°C/min --> 240°C (40 min)
detectorFID, 270°C
integrationpercent concentration calculated from relative peak area


13C-NMR

13C NMR
13C-NMR: (S)-(+)-3-Hydroxybutyric acid ethyl ester
125 MHz, CDCl3
delta [ppm]assignment
13.8CH3 (ethyl ester)
22.3C4
42.8C2
60.3CH2 (ethyl ester)
64.0C3
172.4C1
76.5-77.5CDCl3

IR

IR
IR: (S)-(+)-3-Hydroxybutyric acid ethyl ester
[Film, T%, cm-1]
[cm-1]assignment
3437O-H valence
2979, 2936C-H valence
1735C=O valence, ester

सुकून उतना ही देना प्रभू, जितने से जिंदगी चल जाये। औकात बस इतनी देना, कि औरों का भला हो जाये।
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09b37-misc2b027LIONEL MY SON
He was only in first standard in school when I was hit by a deadly one in a million spine stroke called acute transverse mylitis, it made me 90% paralysed and bound to a wheel chair, Now I keep him as my source of inspiration and helping millions, thanks to millions of my readers who keep me going and help me to keep my son happy
सुकून उतना ही देना प्रभू, जितने से
जिंदगी चल जाये।
औकात बस इतनी देना,
कि औरों का भला हो जाये।



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