4-Methylbenzoyl Chloride → HCID 53783109, compound

HRID 1680267Notes

Reaction equation

HRID 1680267 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14]C)[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[C:13]2[C:8](=[CH:9][C:10]([C:25]([C:24]3[CH:28]=[CH:29][C:21]([CH3:20])=[CH:22][CH:23]=3)=[O:26])=[C:11]([OH:14])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 134054-Methylbenzoyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 14843791Methyl 2,3-dihydro-6-methoxy-1H-indene-1-carboxylate

Product 1

HCID 53783109HCID 53783109, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 20.6 g of 6-methoxy-indane-1-carboxylic acid methyl ester in a little methylene chloride is first slowly added dropwise, at 0° C. to 10° C., to a suspension of 66.8 g of finely powdered aluminium chloride in 100 ml of methylene chloride, which is being stirred under anhydrous conditions; 46.3 g of p-methylbenzoyl chloride are then added dropwise under such conditions that the reaction mixture boils gently under reflux. After completion of the addition, the mixture is heated to the boil for a further 31/2 hours. It is then allowed to cool to room temperature, poured onto 500 g of ice and extracted with twice 500 ml of methylene chloride. The organic phases are washed until neutral, dried over sodium sulphate and evaporated in vacuo (finally in a high vacuum). The evaporation residue, when crystallised from cold ether-petroleum ether, gives 5-(p-toluoyl)-6-hydroxyindane-1-carboxylic acid methyl ester which after a further crystallisation from ethanol-petroleum ether, melts at 74°-76° C.

Workup

  1. temperatureunder reflux
  2. additionAfter completion of the addition
  3. temperaturethe mixture is heated to the boil for a further 31/2 hours
  4. extractionextracted with twice 500 ml of methylene chloride
  5. washThe organic phases are washed until neutral,
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo (finally in a high vacuum)
  8. customThe evaporation residue, when crystallised from cold ether-petroleum ether

Sources & evidence

ORD record
ord-4e17c95330064cfe8d4fe136bd92308e
Source dataset
uspto-grants-1981_06
Patent number
US04272547

Reaction notes

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