Dimethylformamide → 4-Benzyloxybenzoylchloride

HRID 1518284Notes

Reaction equation

HRID 1518284 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>C(Cl)Cl>[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-Benzyloxybenzoylchloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-(Benzyloxy)benzoic acid (4.73 g, 20.72 mmol) was suspended in CH2Cl2 (50 mL). The suspension was cooled to 0° C. To this suspension was added oxalyl chloride (3.63 mL, 41.4 mmol) followed by N,N-dimethylformamide (0.24 mL, 3.11 mmol) dropwise. The reaction was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure, diluted with toluene, and concentrated under reduced pressure. The isolated solid was used directly for the next reaction without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with toluene
  3. concentrationconcentrated under reduced pressure
  4. customThe isolated solid was used directly for the next reaction without further purification

Sources & evidence

ORD record
ord-edceea7f387147f086b9caccde7e0bfb
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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