Hexadecanolide → 16-Hydroxyhexadecanoic acid

HRID 1441145

Reaction equation

HRID 1441145 reaction equation
[C:1]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:19].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[OH:19][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:17])=[O:18]

Participants

5

Reactant 2

HCID 7984HexadecanolideHCID 14798Sodium Hydroxide

Product 1

HCID 1046616-Hydroxyhexadecanoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

A 5 liter three neck round bottom flask, equipped with a mechanical stirrer and reflux condenser, was charged with 300 g (1.16 moles) of 99% hexadecanolide, 1000 mls of 50% sodium hydroxide, 1500 mls of toluene and 5.6 g (0.01 6 moles) of 97% tetrabutylammonium hydrogen sulfate. The reaction mixture stirred at 85°-95° C. overnight, the reaction was cooled, and filtered under vacuum. The filtered solid was washed with diethyl ether before being added to water and acidified to pH=1.5 with concentrated hydrochloric acid. The precipitated product was filtered under vacuum, washed several times with water and dried at 50°-60° C. under high vacuum to give 353 g (1.2 moles) of 97% 16-hydroxy hexadecanoic acid.

Workup

  1. temperaturereflux condenser
  2. temperaturethe reaction was cooled
  3. filtrationfiltered under vacuum
  4. washThe filtered solid was washed with diethyl ether
  5. additionbefore being added to water
  6. filtrationThe precipitated product was filtered under vacuum
  7. washwashed several times with water
  8. customdried at 50°-60° C. under high vacuum

Sources & evidence

ORD record
ord-eae2711375c04c9e88e9de3c726c2df3
Source dataset
uspto-grants-1996_03
Patent number
US05502226

Linked notes

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