Benzene → 2-Ethyl-2-phenyl-5-methoxy-6,7-dichloro-1-indanone

HRID 2052038Notes

Reaction equation

HRID 2052038 reaction equation
C[O-].[Na+].[C:4]1([CH:10]2[CH2:18][C:17]3[C:12](=[C:13]([Cl:22])[C:14]([Cl:21])=[C:15]([O:19][CH3:20])[CH:16]=3)[C:11]2=[O:23])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH2:25][CH3:26].C1C=CC=CC=1>O.CN(C)C=O>[CH2:25]([C:10]1([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:18][C:17]2[C:12](=[C:13]([Cl:22])[C:14]([Cl:21])=[C:15]([O:19][CH3:20])[CH:16]=2)[C:11]1=[O:23])[CH3:26]

Participants

7

Reactant 4

HCID 241BenzeneHCID 6340IodoethaneHCID 10942334Sodium MethoxideHCID 109904442-Phenyl-5-methoxy-6,7-dichloro-1-indanone

Product 1

HCID 124235892-Ethyl-2-phenyl-5-methoxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium methoxide (1.24 g., 0.023 mole) is added portionwise to a stirred mixture of 2-phenyl-5-methoxy-6,7-dichloro-1-indanone (4.61 g., 0.015 mole), iodoethane (15.5 ml., 0.15 mole), benzene (60 ml.) and dimethylformamide (60 ml.) under nitrogen in an ice-water bath. The reaction mixture is left to come to ambient temperature over one hour, then poured into water (1 l.), the benzene layer separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 3.23 g. of 2-ethyl-2-phenyl-5-methoxy-6,7-dichloro-1-indanone which melts at 139°-141° C. on crystallization from benzene:hexane, 1:1.

Workup

  1. waitThe reaction mixture is left
  2. customthe benzene layer separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give 3.23 g
  6. customof 2-ethyl-2-phenyl-5-methoxy-6,7-dichloro-1-indanone which melts at 139°-141° C. on crystallization from benzene

Sources & evidence

ORD record
ord-6d7b9c41fbc143fe8b51fadf94aadfa9
Source dataset
uspto-grants-1980_01
Patent number
US04182764

Reaction notes

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