Hydrochloric Acid → HCID 178496940, compound

HRID 1248344Notes

Reaction equation

HRID 1248344 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][O:6][C:7]([C:9]1[C:12]2[CH:13]=[C:14]([O:17]C)[CH:15]=[CH:16][C:11]=2[CH:10]=1)=[O:8].[CH3:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[S:24].Cl>ClCCl.O>[CH3:5][O:6][C:7]([C:9]1[C:12]2[CH:13]=[C:14]([OH:17])[C:15]([C:23](=[S:24])[C:22]3[CH:26]=[CH:27][CH:28]=[C:20]([CH3:19])[CH:21]=3)=[CH:16][C:11]=2[CH:10]=1)=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 20279433HCID 20279433, compoundHCID 541184135-Methoxybenzocyclobutene-1-carboxylic acid methyl ester

Product 1

HCID 178496940HCID 178496940, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

28.26 g of aluminium trichloride are suspended in 70 ml of dichloromethane and, over a period of 15 minutes, 10.19 g of 5-methoxybenzocyclobutene-1-carboxylic acid methyl ester are added dropwise at from 20° to 30°. Stirring is carried out for 30 minutes, 20.8 g of m-methylthiobenzoyl chloride are added dropwise over a period of 20 minutes and the whole is stirred for 4 hours at room temperature, poured into a mixture of 200 g of ice, 20 ml of concentrated hydrochloric acid and 200 ml of water, stirred for 30 minutes and extracted by shaking twice with 50 ml of dichloromethane each time and once with 50 ml of a mixture of trichloromethane and methanol (3:1). The organic phases are combined, washed twice with water, dried over magnesium sulphate, treated with kieselguhr and concentrated by evaporation. Chromatography over silica gel using hexane/ethyl acetate (4:1) as eluant yields 4-(m-methylthiobenzoyl)-5-hydroxybenzocyclobutene-1-carboxylic acid methyl ester in the form of a yellow oil.

Workup

  1. stirringthe whole is stirred for 4 hours at room temperature
  2. stirringstirred for 30 minutes
  3. extractionextracted
  4. stirringby shaking twice with 50 ml of dichloromethane each time
  5. washwashed twice with water
  6. dry with materialdried over magnesium sulphate
  7. additiontreated with kieselguhr
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2bc3d39e710444dfb46fb01455af0624
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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