Acetyl chloride → HCID 19388988, compound

HRID 1110266Notes

Reaction equation

HRID 1110266 reaction equation
C1(C[O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([OH:35])[CH:11]=2)C=CC=CC=1.C(N(CC)CC)C.[C:44](Cl)(=[O:46])[CH3:45]>C(Cl)Cl>[C:44]([O:35][C:12]1[CH:11]=[C:10]([C:9]([OH:8])=[O:36])[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=1)(=[O:46])[CH3:45]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 152334763-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester

Product 1

HCID 19388988HCID 19388988, compoundYield 115.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and ice bath cooled solution of 5.0 g (0.01 mol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester in 7.5 ml of methylene chloride and 2.8 ml (0.02 mol) of triethylamine was added 0.86 ml (0.012 mol of acetyl chloride. The reaction mixture was stirred in an ice bath for 1 hour, at room temperature for 2 hours and then was washed with 1N HCl, with NaHCO3 solution, dried and concentrated at reduced pressure to a solid. Trituration with methanol and filtration gave 5.17 g (96% yield, mp 55°-56°) of 3-acetyloxy-5-(octadecyloxy)benzenecarboxylic acid.

Workup

  1. stirringThe reaction mixture was stirred in an ice bath for 1 hour, at room temperature for 2 hours
  2. washwas washed with 1N HCl, with NaHCO3 solution
  3. customdried
  4. concentrationconcentrated at reduced pressure to a solid
  5. filtrationTrituration with methanol and filtration

Sources & evidence

ORD record
ord-493e28c0cf5f4c98aa0699c2e40bb989
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

Loading…