2,3-Dichloro-4-(2-phenylacryloyl)anisole → 2-Phenyl-5-methoxy-6,7-dichloro-1-indanone

HRID 1447667Notes

Reaction equation

HRID 1447667 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:18])[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH2:11])[CH:5]=[CH:4][C:3]=1[O:19][CH3:20]>S(=O)(=O)(O)O>[C:12]1([CH:10]2[CH2:11][C:5]3[C:6](=[C:7]([Cl:8])[C:2]([Cl:1])=[C:3]([O:19][CH3:20])[CH:4]=3)[C:9]2=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 1

HCID 109248102,3-Dichloro-4-(2-phenylacryloyl)anisole

Product 1

HCID 109904442-Phenyl-5-methoxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2,3-Dichloro-4-(2-phenylacryloyl)anisole (7.4 g., 0.024 mole) is added portionwise to cold, concentrated sulfuric acid (150 ml.) with stirring. The reaction mixture is stirred in an ice bath for 2 hours, then added dropwise to ice-water to precipitate 3.91 g. of 2-phenyl-5-methoxy-6,7-dichloro-1-indanone which melts at 193°-195° C. upon crystallization from benzene:cyclohexane, 1:2.

Workup

  1. stirringThe reaction mixture is stirred in an ice bath for 2 hours
  2. customto precipitate 3.91 g
  3. customof 2-phenyl-5-methoxy-6,7-dichloro-1-indanone which melts at 193°-195° C. upon crystallization from benzene

Sources & evidence

ORD record
ord-6e3982ef4e66447890a07c7dcbea2422
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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