Dimethylformamide → 2-Ethoxybenzoyl chloride

HRID 2353793Notes

Reaction equation

HRID 2353793 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9](CCCCCCCCCCCCCCC)[C:5]=1[C:6](O)=[O:7])[CH3:2].S(Cl)([Cl:30])=O.CN(C)C=O>CCCCCC>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([Cl:30])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 684514982-Ethoxy-6-pentadecylbenzoic Acid

Product 1

HCID 30163972-Ethoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred solution of 2-Ethoxy-6-pentadecylbenzoic Acid (6.5 g, 16 mmol) in hexane (60 mL) were added thionyl chloride (2.5 g, 21 mmol) and N,N-dimethylformamide (0.5 mL). The reaction mixture was heated to reflux for 1 h. After the reaction was complete, the solvent was evaporated under reduced pressure to yield the desired 2-Ethoxy-benzoyl Chloride, which was redissolved in dichloromethane (50 mL) and used for the condensation with anilides.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f137194579e848fb952ccb074cc195bf
Source dataset
uspto-grants-2010_07
Patent number
US07750047B2

Reaction notes

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