2-(4-Methoxyphenyl)-2-methyl-5-benzyloxy-6,7-dichloro-1-indanone → 2-(4-Methoxyphenyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone

HRID 1447674Notes

Reaction equation

HRID 1447674 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:29])[CH2:17][C:16]3[C:11](=[C:12]([Cl:27])[C:13]([Cl:26])=[C:14]([O:18]CC4C=CC=CC=4)[CH:15]=3)[C:10]2=[O:28])=[CH:5][CH:4]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:29])[CH2:17][C:16]3[C:11](=[C:12]([Cl:27])[C:13]([Cl:26])=[C:14]([OH:18])[CH:15]=3)[C:10]2=[O:28])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 124236152-(4-Methoxyphenyl)-2-methyl-5-benzyloxy-6,7-dichloro-1-indanone

Product 1

HCID 124236162-(4-Methoxyphenyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-Methoxyphenyl)-2-methyl-5-benzyloxy-6,7-dichloro-1-indanone (3.44 g., 0.008 mole) is catalytically hydrogenated in absolute ethanol (300 ml.) over 5% palladium on carbon (500 mg.) in a Parr apparatus at 25° C. for 4 hrs. The reaction mixture is filtered and concentrated in vacuo to give 2.6 g. of 2-(4-methoxyphenyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone which melts at 149°-156° C. and is used without further purification.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated in vacuo
  3. customto give 2.6 g
  4. customof 2-(4-methoxyphenyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone which melts at 149°-156° C. and is used without further purification

Sources & evidence

ORD record
ord-81588075578245ae87d3cf505de3ceb6
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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