2-Methylene-2',3'-dichloro-4'-methoxypropiophenone → 2-Methyl-5-methoxy-6,7-dichloro-1-indanone

HRID 1283245Notes

Reaction equation

HRID 1283245 reaction equation
[CH2:1]=[C:2]([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([Cl:13])[C:6]=1[Cl:14])=[O:4]>S(=O)(=O)(O)O>[CH3:1][CH:2]1[CH2:15][C:10]2[C:5](=[C:6]([Cl:14])[C:7]([Cl:13])=[C:8]([O:11][CH3:12])[CH:9]=2)[C:3]1=[O:4]

Participants

3

Reactant 1

HCID 123955602-Methylene-2',3'-dichloro-4'-methoxypropiophenone

Product 1

HCID 123955612-Methyl-5-methoxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-methylene-2',3'-dichloro-4'-methoxypropiophenone (40 g., 0.163 mole) in concentrated sulfuric acid (75 ml.) is allowed to stand at 25°C. for 24 hours and then is slowly poured into vigorously stirred ice water (500 ml.). The 2-methyl-5-methoxy-6,7-dichloro-1-indanone (VI) which separate (40 mg.) melts at 129°C. after recrystallization from methylcyclohexane.

Workup

  1. customThe 2-methyl-5-methoxy-6,7-dichloro-1-indanone (VI) which separate (40 mg.) melts at 129°C.
  2. customafter recrystallization from methylcyclohexane

Sources & evidence

ORD record
ord-c16675bd74fc4e42a66eda1472ac12ca
Source dataset
uspto-grants-1976_08
Patent number
US03974212

Reaction notes

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