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

HRID 596554Notes

Reaction equation

HRID 596554 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 one 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-2514216a18514283ba4a2868bceff69e
Source dataset
uspto-grants-1977_03
Patent number
US04011258

Reaction notes

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