Hydrochloric Acid → 3-Benzyloxybenzoyl chloride

HRID 1484492Notes

Reaction equation

HRID 1484492 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:21])=O.Cl>CN(C)C=O.ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([Cl:21])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 3092263-(Benzyloxy)benzoic acid

Product 1

HCID 49953753-Benzyloxybenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 3-benzyloxybenzoic acid (22.0 g; 0.096 mol) and dry dimethylformamide (2 drops) in dry dichloromethane (100 cm3) was treated with oxalyl chloride (19 g; 0.15 mol) which was added in 4 approximately equal portions over ˜30 minutes. The mixture was stirred at room temperature until evolution of hydrogen chloride had ceased (˜6 hrs). The resulting colourless solution was evaporated in vacuo at 40° to constant weight to give a very pale tan oil that solidified rapidly to give the title compound as off-white needles.

Workup

  1. additionwas added in 4 approximately equal portions over ˜30 minutes
  2. custom(˜6 hrs)
  3. customThe resulting colourless solution was evaporated in vacuo at 40° to constant weight
  4. customto give a very pale tan oil that

Sources & evidence

ORD record
ord-841db09304a443bd902c4956e9a9706b
Source dataset
uspto-grants-2016_08
Patent number
US09422253B2

Reaction notes

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