Benzoyl chloride → HCID 54109752, compound

HRID 1680263Notes

Reaction equation

HRID 1680263 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]([CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18]C)[CH:16]=2)[CH2:11][CH2:10]1)=[O:8].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:5][O:6][C:7]([CH:9]1[C:17]2[C:12](=[CH:13][C:14]([C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10]1)=[O:8]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14843791Methyl 2,3-dihydro-6-methoxy-1H-indene-1-carboxylate

Product 1

HCID 54109752HCID 54109752, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 g of finely powdered aluminium chloride are added in portions to a stirred solution of 20.6 g of 6-methoxy-indane-1-carboxylic acid methyl ester and 15.5 g of benzoyl chloride in 200 ml of absolute methylene chloride at 20° C., in an anhydrous atmosphere, stirring is continued overnight at room temperature and the reaction solution is then poured onto 500 g of ice and extracted with 3 times 100 ml of methylene chloride. The organic phases are washed successively with 500 ml of saturated sodium bicarbonate solution, 500 ml of 2 N hydrochloric acid and 500 ml of water, dried over anhydrous sodium sulphate and evaporated in vacuo. The evaporation residue, when crystallised from ether-petroleum ether after treatment with active charcoal, gives 5-benzoyl-6-hydroxy-indane-1-carboxylic acid methyl ester of melting point 89°-91° C.

Workup

  1. extractionextracted with 3 times 100 ml of methylene chloride
  2. washThe organic phases are washed successively with 500 ml of saturated sodium bicarbonate solution, 500 ml of 2 N hydrochloric acid and 500 ml of water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated in vacuo
  5. customThe evaporation residue, when crystallised from ether-petroleum ether after treatment with active charcoal

Sources & evidence

ORD record
ord-d89173f0fe0f45be8ead242a1b5dd5e5
Source dataset
uspto-grants-1981_06
Patent number
US04272547

Reaction notes

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