3,5-Dichlorobenzoic acid → 3,5-Dichlorobenzoyl chloride

HRID 904095

Reaction equation

HRID 904095 reaction equation
[Cl:1]C1C=C(C=C(Cl)C=1)C(C)=C.S(Cl)(Cl)=O.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[C:20](O)=[O:21]>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[C:20]([Cl:1])=[O:21]

Participants

4

Reactant 3

HCID 58113,5-Dichlorobenzoic acidHCID 24386Thionyl ChlorideHCID 1106043,5-Dichloro-alpha-methylstyrene

Product 1

HCID 761913,5-Dichlorobenzoyl chloride

Procedure

It has been known that 3,5-dichloro-α-methylstyrene can be produced by reacting thionyl chloride with 3,5-dichlorobenzoic acid to obtain 3,5-dichlorobenzoyl chloride and then reacting methanol with 3,5-dichlorobenzoyl chloride to obtain methyl-3,5-dichlorobenzoate and reacting methylmagnesium chloride with methyl-3,5-dichlorobenzoate in ether and then, hydrolyzing the product with a diluted hydrochloric acid and dehydrating the product over sodium bisulfate, in for example, Journal of the American Chemical Society 73 January 1951, page 455-456. However, this process is not advantageous as an industrial process because many reaction steps are needed for producing methyl3,5-dichlorobenzoate and a complicated reaction step is included in these steps for producing the starting material and the hydrolysis and the dehydration should be separately carried out.

Workup

  1. customcan be produced

Sources & evidence

ORD record
ord-4c21f5935dea4e088905616f3b1cbb8d
Source dataset
uspto-grants-1980_10
Patent number
US04230642

Linked notes

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