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

HRID 359805Notes

Reaction equation

HRID 359805 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-829894dc099c4f129997eb0442b28e22
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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