Thionyl Chloride → 4-(6-Bromohexyloxy)benzoyl chloride

HRID 2165390Notes

Reaction equation

HRID 2165390 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1.S(Cl)([Cl:20])=O>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([Cl:20])=[O:14])=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 20064021HCID 20064021, compound

Product 1

HCID 200639874-(6-Bromohexyloxy)benzoyl chloride

Procedure

A mixture of 452 g of 4-(6-bromohexyloxy)benzoic acid and 1000 g of thionyl chloride was stirred at room temperature for about 20 hours. The reaction mixture was concentrated in vacuo and residual thionyl chloride removed by repeated addition of toluene and concentration in vacuo. The oily product comprising 4-(6-bromohexyloxy)benzoyl chloride (450 ml) was used directly in the next reaction.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and residual thionyl chloride
  2. customremoved
  3. additionaddition of toluene and concentration in vacuo
  4. customThe oily product comprising 4-(6-bromohexyloxy)benzoyl chloride (450 ml) was used directly in the next reaction

Sources & evidence

ORD record
ord-b57962b008124058811d7136199c57ea
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

Loading…