Dicyclohexylamine → p-Acetoxybenzoyl chloride

HRID 584973Notes

Reaction equation

HRID 584973 reaction equation
C1(NC2CCCCC2)CCCCC1.[C:14]([O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)(=[O:16])[CH3:15].S(Cl)([Cl:29])=O>ClCCl.C(OCC)C>[C:14]([O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([Cl:29])=[O:23])=[CH:20][CH:19]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 7582DicyclohexylamineHCID 16865Benzoic acid, 4-(acetyloxy)-HCID 24386Thionyl Chloride

Product 1

HCID 2756254p-Acetoxybenzoyl chloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1.1 ml (5.6 mmol) of dicyclohexylamine are added to 1 g (5.6 mmol) of 4-acetoxybenzoic acid placed in 10 ml of dichloromethane, and the solution is stirred at room temperature for minutes. 400 μl (5.6 mmol) of thionyl chloride are added and this mixture is stirred at room temperature for 2 hours. The reaction medium is diluted with ethyl ether. The precipitate is filtered off and rinsed with ethyl ether. Concentration of the filtrate gives the 4-acetoxybenzoyl chloride.

Workup

  1. stirringthis mixture is stirred at room temperature for 2 hours
  2. filtrationThe precipitate is filtered off
  3. washrinsed with ethyl ether

Sources & evidence

ORD record
ord-6b525bc01e5d499b93d1947d82fb90c1
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

Loading…