Tetrahydrofuran → 3-Chloro-4-methoxybenzoyl chloride

HRID 1683838Notes

Reaction equation

HRID 1683838 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5](O)=[O:6].O1CCCC1.C(Cl)(=O)C([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([Cl:21])=[O:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 1699823-Chloro-p-anisic acid

Product 1

HCID 47692993-Chloro-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution of 0.22 gram (0.0012 mole) of 3-chloro-4-methoxybenzoic acid in a small amount of tetrahydrofuran and chloroform was cooled to 0° C., and 0.12 mL (0.0014 mole) of oxalyl chloride was added dropwise. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature, where it was stirred for about 3.5 hours. After this time the reaction mixture was concentrated under reduced pressure, yielding 3-chloro-4-methoxybenzoyl chloride, which was dissolved in a small amount of tetrahydrofuran for later use.

Workup

  1. additionUpon completion of addition
  2. concentrationAfter this time the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0486d7e71bd341848c7455704c1e7c5c
Source dataset
uspto-grants-1997_06
Patent number
US05639763

Reaction notes

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