Cyclohexane → Indacrinone

HRID 839701Notes

Reaction equation

HRID 839701 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH3:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1CCCCC1>C1C=CC=CC=1.CS(O)(=O)=O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH3:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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-9b6fb8647ee448b6890fe50d8005cfe1
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

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