Dimethylformamide → 2-Methyl-2-phenyl-5-methoxy-6,7-dichloro-1-indanone

HRID 1287517Notes

Reaction equation

HRID 1287517 reaction equation
[C:1]1([CH:7]2[CH2:15][C:14]3[C:9](=[C:10]([Cl:19])[C:11]([Cl:18])=[C:12]([O:16][CH3:17])[CH:13]=3)[C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21]N(C=O)C.O(C)[Na].IC>O.C1C=CC=CC=1>[CH3:21][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:15][C:14]2[C:9](=[C:10]([Cl:19])[C:11]([Cl:18])=[C:12]([O:16][CH3:17])[CH:13]=2)[C:8]1=[O:20]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 109904442-Phenyl-5-methoxy-6,7-dichloro-1-indanoneHCID 178418582HCID 178418582, compound2×

Product 1

HCID 124235872-Methyl-2-phenyl-5-methoxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

2-Phenyl-5-methoxy-6,7-dichloro-1-indanone, 50.84 g. is dissolved in 700 ml. dry DMF and 700 ml. benzene in a 3-liter flask equipped with a nitrogen inlet, air condenser and hopper for NaOCH3. The reaction mixture is cooled in ice-water and 103 ml. of iodomethane is added. NaOCH3, 13.5 g., is added portion wise from the hopper over 3/4 of an hour. After stirring for 1/2 hour in an ice-water bath, the reaction mixture is added to water, (4 liters), and extracted with benzene. The benzene layer is separated dried over molecular sieves and concentrated to dryness to give 2-methyl-2-phenyl-5-methoxy-6,7-dichloro-1-indanone, mp 164°-5°C. after recrystallization from benzene-cyclohexane, 1:2.

Workup

  1. dissolutionis dissolved in 700 ml
  2. addition, is added portion wise from the hopper over 3/4 of an hour
  3. extractionextracted with benzene
  4. customThe benzene layer is separated
  5. customdried over molecular sieves
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bb956eb8e5b44e47b05a19f67e3045be
Source dataset
uspto-grants-1976_10
Patent number
US03984552

Reaction notes

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