Hydrochloric Acid → 3-Chloro-4-methoxybenzoyl chloride

HRID 1283641

Reaction equation

HRID 1283641 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([Cl:12])[CH:5]=1.[OH-].[Na+].[ClH:16]>O>[Cl:12][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][CH3:11])[C:3]([Cl:16])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 123469Methyl 3-chloro-p-anisate

Product 1

HCID 47692993-Chloro-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.4 g. (0.052 mol.) of 3-chloro-4-methoxybenzoic acid methyl ester and 3.5 g. (0.09 mol.) of sodium hydroxide in 150 ml. of water was refluxed for two hours. The reaction mixture was cooled and acidified with 10% aqueous hydrochloric acid to precipitate 3-chloro-4-methoxybenzoic acid, m.p. 199°-202°. The acid was refluxed with thionyl chloride as described in the procedure of Example 9 to give 3-chloro-4-methoxybenzoic acid chloride, m.p. 55°-57°.

Workup

  1. additionA mixture of 10.4 g
  2. temperatureThe reaction mixture was cooled
  3. customto precipitate 3-chloro-4-methoxybenzoic acid, m.p. 199°-202°
  4. temperatureThe acid was refluxed with thionyl chloride

Sources & evidence

ORD record
ord-3d84c3f678a24b7e9b92c4cbcf018d63
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Linked notes

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