Acetic Acid → HCID 20322229, compound

HRID 1833766Notes

Reaction equation

HRID 1833766 reaction equation
[N+](=C)=[N-].[C:4]([CH:7]([CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])(=[O:6])[CH3:5].[C:27](O)(=O)C>CCOCC>[C:4]([CH:7]([CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:27])=[O:15])(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 12042400Heptadecanoic acid, 8-acetyl-12-hydroxy-

Product 1

HCID 20322229HCID 20322229, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of diazomethane (approx. 2.5 g., 0.06 mole) in order (100 ml.) is mixed with a solution of 8-acetyl-12-hydroxyheptadecanoic acid (9.9 g., 0.03 mole) in ether (50 ml.). The resulting solution is allowed to stand 4 hours at room temperature. Acetic acid is then added to destroy the excess diazomethane and the solution is washed with dilute sodium bicarbonate solution and water and dried over sodium sulfate. Evaporation of volatile materials at reduced pressure yields methyl 8-acetyl-12-hydroxyheptadecanoate, a colorless viscous oil.

Workup

  1. customto destroy the excess diazomethane
  2. washthe solution is washed with dilute sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of volatile materials at reduced pressure

Sources & evidence

ORD record
ord-6c3934be071847afbc73a7d169a97fce
Source dataset
uspto-grants-1978_01
Patent number
US04066692

Reaction notes

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