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

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

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

fermenting yeast sucrose

; 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
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	F Xn N		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

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

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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