Dimethylformamide → 4-Benzyloxybenzoylchloride

HRID 270964Notes

Reaction equation

HRID 270964 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:21])=O.CN(C)C=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([Cl:21])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 738804-(Benzyloxy)benzoic acid

Product 1

HCID 37664104-BenzyloxybenzoylchlorideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5.0 g (21.9 mmol) of 4-benzyloxy-benzoic acid in 25 mL of dichloromethane (DCM) was added dropwise 10 mL (114 mmol) of oxalyl chloride, followed by 5 □L of dimethylformamide (DMF cat) and the reaction mixture was heated at reflux for 3 h, and concentrated to give 5.32 g (98%) of desired 4-benzyloxy-benzoyl chloride as a yellow solid as indicated by 1H NMR. The product was used without any further purification in the next step.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2ee35eb0b95c4f349756849e71b35b84
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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