Synthesis of erythro-9,10-dihydroxystearic acid, ارثرو-10،9-ثنائي هيدروحامض الستيارك, erythro-9,10-Διυδροστεατικό οξ

Erythro-9,10-Dihydroxystearic acid [3639-32-5]



Name erythro-9,10-Dihydroxystearic acid
Synonyms (9R,10S)-rel-9,10-Dihydroxyoctadecanoic acid
Name in Chemical Abstracts Octadecanoic acid, 9,10-dihydroxy-, (9R,10S)-rel-
CAS No 3639-32-5
EINECS No
Molecular formula C18H34O4
Molecular mass 330.51

KMnO4/NaOH

Literature
A. Lapworth und E. N. Mottram, J. Chem. Soc., 1925,1628-31

http://kriemhild.uft.uni-bremen.de/nop/en/instructions/pdf/3011_en.pdf

Reaction type:	addition to alkenes, oxidation, cis-hydroxylation
Substance classes:	alkene, alcohol, natural product
Techniques:	stirring with magnetic stir bar, filtering, recrystallizing, extracting

Instruction (batch scale 10 mmol) 

Equipment 

5 L beaker or Erlenmeyer flask, heatable magnetic stirrer, magnetic stir bar, suction flask, 

Buechner funnel, mortar, desiccator 

Substances 

oleic acid (techn. 90%) 3.14 g (equivalent to 10.0 mmol pure oleic acid) 

(oleic acid, pure: mp 16 °C, 

bp 193 °C/1.6 hPa) 

potassium permanganate 2.50 g (15.8 mmol) 

sodium hydroxid 3.14 g (78.5 mmol) 

hydrochloric acid (conc., 36%) 94 mL 

sodium sulfite or sodium disulfite 

petroleum ether (bp 60-80 °C) about 200 mL 

ethanol (bp 78 °C) for recrystallizing 

Reaction 

3.14 g (10.0 mmol) oleic acid (techn. 90%) are added to a solution of 3.14 g (78.5 mmol) 

NaOH in 320 mL water in a 5 L beaker with a magnetic stir bar. The mixture is heated under

stirring until a clear solution is formed. After the addition of 2.5 L ice-cold water, 250 mL 1% 

potassium permanganate solution are added within 1 minute under stirring at a temperature of 

10 °C. After 5 minutes so much solid sodium sulfite oder sodium disulfite is added, that the 

excess of potassium permanganate is reduced. Afterwards the solution is acidified with 94 mL 

conc. hydrochloric acid. The solution becomes colourless, and a colourless fluffy precipitation 

is formed. 

Work up 

The precipitation is sucked off and dried. Crude yield: 3.01 g, mp 81-88 °C 

The crude product is washed with 50 mL petroleum ether (60-80 °C) and dried under reduced 

pressure. The dried product is powdered in a mortar and digested with 100-150 mL petroleum 

ether in a beaker. Thus the sturated carboxylic acids contained in the oleic acid as impurities 

are removed. The dihydroxystearic acid is insoluble in petroleum ether. It is sucked off and 

recrystallized from ethanol. 

Yield: 2.74 g (8.70 mmol, 87%); mp 132 °C; colourless powder 

Yield71%Target product mass0.26gSum of input masses290gMass efficiency0.89mg/gMass index1100g input / g productE factor1100g waste / g product

Equipment

Batch scale:

0.0011 mol

	beaker 500 mL			heatable magnetic stirrer with magnetic stir bar
	suction flask			suction filter
	mortar			exsiccator with drying agent

TLC: crude product
TLC layer	Merck silica gel 60 F254
mobile phase	EtOAc
detection	immerse into solution of 2.7 g KMnO4, 18 g K2CO3, 216 mg NaOH in 274 mL H2O, heating with air dryer
Rf (educt)	0.87
Rf (product)	0.67

1H-NMR: erythro-9,10-Dihydroxystearic acid
250 MHz, DMSO-d6
delta [ppm]	mult.	atoms	assignment
0.86	t (3J = 6.4 Hz)	3 H	CH3
1.2-1.6	m	26 H	other CH2
2.18	t (3J = 7.3 Hz)	2 H	2-CH2
3.25	m	2 H	9-CH-OH, 10-CH-OH
2.45	s	6 H	DMSO

13C-NMR: erythro-9,10-Dihydroxystearic acid
62.5 MHz, DMSO-d6, 373°K
delta [ppm]	assignment
13.0	C18 (CH3)
21.2	C17 (CH2
23.9	CH2
24.8	CH2
27.9	CH2
28.0	CH2
28.3	CH2
28.4	CH2
28.6	CH2
30.6	CH2
31.8	CH2
33.2	C2
73.4	C9, C10 (CH-OH)
173.4	C1 (COOH)
38.5-40.5	DMSO-d6

IR: erythro-9,10-Dihydroxystearic acid
[KBr, T%, cm-1]
[cm-1]	assignment
3500-2500	O-H valence, superimposed on C-H valence
1716	C=O valence, carboxylic acid