Hydrochloric Acid → HCID 13662991, compound

HRID 648028Notes

Reaction equation

HRID 648028 reaction equation
O[CH2:2][C:3]1[CH:15]=[CH:14][C:6]2[S:7][C:8]([C:11]([OH:13])=[O:12])=[C:9]([CH3:10])[C:5]=2[CH:4]=1.[ClH:16].[CH3:17]O>>[CH3:17][O:13][C:11]([C:8]1[S:7][C:6]2[CH:14]=[CH:15][C:3]([CH2:2][Cl:16])=[CH:4][C:5]=2[C:9]=1[CH3:10])=[O:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13540118HCID 13540118, compound

Product 1

HCID 13662991HCID 13662991, compound

Procedure

5-Hydroxymethyl-3-methylbenzo[b]thiophene-2-carboxylic acid (4.4 g.) was dissolved in methanol (150 ml.) and the solution was saturated with hydrogen chloride gas. It was then heated under reflux for 4 hours and cooled. The solid which crystallized out was filtered off and dried. The product (3.54 g.) was shown by n.m.r. to consist of a mixture of 5-chloromethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester (65%) and 5-methoxymethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester. The product was chromatographed on silica gel. Elution with toluene first gave 5-chloromethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester, m.p. 115°-116° C. (from petrol b.p. 40°-60° C.).

Workup

  1. temperatureIt was then heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. customThe solid which crystallized out
  5. filtrationwas filtered off
  6. customdried
  7. additionto consist of a mixture of 5-chloromethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester (65%) and 5-methoxymethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester
  8. customThe product was chromatographed on silica gel
  9. washElution with toluene first gave 5-chloromethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester, m.p. 115°-116° C. (from petrol b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-e8c0aafbb84844618f6e4baff3744f03
Source dataset
uspto-grants-1983_10
Patent number
US04410539

Reaction notes

Loading…