Water → HCID 12395657, compound

HRID 1679749Notes

Reaction equation

HRID 1679749 reaction equation
[CH2:1]([CH:3]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[C:6]([Cl:21])[C:7]([Cl:20])=[C:8]([O:18][CH3:19])[CH:9]=2)[C:4]1=[O:22])[CH3:2].[CH3:23]I.C[O-].[Na+].O>CN(C)C=O.C1C=CC=CC=1>[CH2:1]([C:3]1([CH3:23])[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[C:6]([Cl:21])[C:7]([Cl:20])=[C:8]([O:18][CH3:19])[CH:9]=2)[C:4]1=[O:22])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 12395569HCID 12395569, compound

Product 1

HCID 12395657HCID 12395657, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

2-Ethyl-3-phenyl-6,7-dichloro-5-methoxy-1-indanone (10.05 g., 0.03 mole) and methyl iodide (12.5 ml., 0.2 mole) dissolved in dimethylformamide (100 ml.)-benzene (100 ml.) at 0° C. under nitrogen are treated portionwise with sodium methoxide (3.54 g., 0.033 mole) over a 30 minute period. The reaction mixture is stirred in an ice-water bath for one hour, then poured into water (500 ml.), extracted with benzene, the organic layer separated, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness to give an oily residue which on trituration with hexane gives 7.64 g. (71%) of 2-ethyl-2-methyl-3-phenyl-6,7-dichloro-5-methoxy-1-indanone which melts at 132° C. on crystallization from cyclohexane.

Workup

  1. extractionextracted with benzene
  2. customthe organic layer separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customto give an oily residue which on trituration with hexane
  7. customgives 7.64 g
  8. custom(71%) of 2-ethyl-2-methyl-3-phenyl-6,7-dichloro-5-methoxy-1-indanone which melts at 132° C. on crystallization from cyclohexane

Sources & evidence

ORD record
ord-a442d646d9304cffa545c0acf4277194
Source dataset
uspto-grants-1978_03
Patent number
US04081554

Reaction notes

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