Acetic Acid → Methyl 4-(4-acetyl-8-hydroxytridecyl)benzoate

HRID 26611Notes

Reaction equation

HRID 26611 reaction equation
[N+](=C)=[N-].[C:4]([CH:7]([CH2:20][CH2:21][CH2:22][CH:23]([OH:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)(=[O:6])[CH3:5].[C:30](O)(=O)C>CCOCC>[C:4]([CH:7]([CH2:20][CH2:21][CH2:22][CH:23]([OH:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:30])=[O:16])=[CH:18][CH:19]=1)(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 203860504-(4-Acetyl-8-hydroxytridecyl)benzoic acid

Product 1

HCID 20386072Methyl 4-(4-acetyl-8-hydroxytridecyl)benzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane (approximately 2.5 g., 0.06 mole) in ether (100 ml.) is mixed with a solution of 4-(4-acetyl-8-hydroxytridecyl)benzoic acid (10.8 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 4-(4-acetyl-8-hydroxytridecyl)benzoate, 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-2c63af5457b94fa0bd77f1f3794a6fa2
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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