Thionyl Chloride → 3,5-Bis(benzyloxy)benzoyl chloride

HRID 1578629Notes

Reaction equation

HRID 1578629 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:28])=O>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=1)[C:12]([Cl:28])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 993073,5-Bis(phenylmethoxy)benzoic acid

Product 1

HCID 108318693,5-Bis(benzyloxy)benzoyl chloride

Procedure

167 g of 3,5-dibenzyloxybenzoic acid and 400 ml of redistilled thionyl chloride were refluxed on an oil bath for 1 hour. Excess thionyl chloride was distilled off at reduced pressure, and the remaining mass crystallized. The product was recrystallized from petroleum ether (B.p., 60°-85°C.) : M.P. 73°-74°C.

Workup

  1. distillationExcess thionyl chloride was distilled off at reduced pressure
  2. customthe remaining mass crystallized
  3. customThe product was recrystallized from petroleum ether (B.p., 60°-85°C.)

Sources & evidence

ORD record
ord-25fdc2269fbc4de39071a3220be82b75
Source dataset
uspto-grants-1976_02
Patent number
US03937838

Reaction notes

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