Acetic Acid → Methyl 8-acetyl-8-chloro-12-hydroxyheptadecanoate

HRID 1730230Notes

Reaction equation

HRID 1730230 reaction equation
[N+](=C)=[N-].[C:4]([C:7]([Cl:27])([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:28](O)(=O)C>CCOCC>[C:4]([C:7]([Cl:27])([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][CH3:28])=[O:15])(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 213974028-Acetyl-8-chloro-12-hydroxyheptadecanoic acid

Product 1

HCID 21397381Methyl 8-acetyl-8-chloro-12-hydroxyheptadecanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane (approx. 2.5 g., 0.06 mole) in ether (100 ml.) is mixed with a solution of 8-acetyl-8-chloro-12-hydroxyheptadecanoic acid (10.9 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-8-chloro-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-5ae7fdc950aa4d05ae4f8378affbcb66
Source dataset
uspto-grants-1976_11
Patent number
US03991087

Reaction notes

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