Thionyl Chloride → 3,4-Bis(benzyloxy)benzoyl chloride

HRID 2042394Notes

Reaction equation

HRID 2042394 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]([Cl:28])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 108541553,4-Bis(benzyloxy)benzoic acid

Product 1

HCID 110026733,4-Bis(benzyloxy)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

3,4-dibenzyloxybenzoic acid (3.1 g. 9.3 mmol) was combined with pyridine (5 drops, catalytic) and thionyl chloride (15 ml, 205 mmol). The solution was heated at reflux for 4 h, cooled, and excess thionyl chloride removed under reduced pressure. The crude product was dissolved in benzene (50 ml), and stripped of solvent under vacuum. The benzoyl chloride (theoretical yield 3.4 g) was then dissolved in dichloromethane and used directly in the next step.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 4 h
  3. temperaturecooled
  4. customexcess thionyl chloride removed under reduced pressure
  5. dissolutionThe crude product was dissolved in benzene (50 ml)
  6. dissolutionThe benzoyl chloride (theoretical yield 3.4 g) was then dissolved in dichloromethane

Sources & evidence

ORD record
ord-ca76c8c6764f477699d42cf081fc1b05
Source dataset
uspto-grants-2013_11
Patent number
US08586585B2

Reaction notes

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