Hydrochloric Acid → HCID 54070426, compound

HRID 280615Notes

Reaction equation

HRID 280615 reaction equation
[ClH:1].[CH3:2][O:3][C:4]([C:6]1[C:11]2[S:12][C:13]([CH3:15])=[CH:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:5].[CH2:16]=O>C(Cl)(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[CH3:2][O:3][C:4]([C:6]1[C:11]2[S:12][C:13]([CH3:15])=[C:14]([CH2:16][Cl:1])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 53739261HCID 53739261, compound

Product 1

HCID 54070426HCID 54070426, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6212ChloroformSolvent

Procedure

Hydrogen chloride gas was passed for 30 minutes through a stirred mixture of 2-methylbenzo[b]thiophene-7-carboxylic acid methyl ester (4.50 g), paraformaldehyde (1.23 g) and anhydrous zinc chloride (1.03 g) in chloroform (50 ml). The mixture was stirred at room temperature for 5 hours and then allowed to stand for 18 hours. The mixture was then washed several times with water and the organic layer was dried (Na2SO4) and evaporated. The residue was crystallised from chloroform/petrol (b.p. 60°-80°) to give 3-chloromethyl-2-methylbenzo[b]thiophene-7-carboxylic acid methyl ester (4.10 g), m.p. 125°-126°.

Workup

  1. waitto stand for 18 hours
  2. washThe mixture was then washed several times with water
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. customevaporated
  5. customThe residue was crystallised from chloroform/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-d9c946e7b6e5469084eb32dee9537091
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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