Cyclohexane → Indacrinone

HRID 1447696Notes

Reaction equation

HRID 1447696 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[C:16]([Cl:19])[C:17]=1[Cl:18])[C:14](=[O:20])[C:13]([CH3:27])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:12]2)(C)(C)C.C1CCCCC1>C1C=CC=CC=1.CS(O)(=O)=O>[O:20]=[C:14]1[C:15]2[C:11](=[CH:10][C:9]([O:8][CH2:7][C:6]([OH:28])=[O:5])=[C:17]([Cl:18])[C:16]=2[Cl:19])[CH2:12][C:13]1([CH3:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 8078CyclohexaneHCID 20384375Tert-butyl(1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetate

Product 1

HCID 42266Indacrinone

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 241BenzeneSolvent

Procedure

A solution of tert-butyl(1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetate (1.0 g., 0.00237 mole) in benzene (25 ml.) is treated with methanesulfonic acid (2 drops) and refluxed for 1/2 hour. The reaction mixture is treated with cyclohexane (20 ml.) and cooled affording (1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetic acid which is filtered and dried.

Workup

  1. temperaturerefluxed for 1/2 hour
  2. temperaturecooled

Sources & evidence

ORD record
ord-2def9eb20cd04097a2ae1235f2bd99e5
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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