Benzyl Chloride → 4-(benzyloxy)-2,3-dihydro-1H-inden-1-one

HRID 1388294

Reaction equation

HRID 1388294 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.O>[C:19]1([CH2:18][O:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][C:6]3=[O:11])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 136161924-(benzyloxy)-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.44 g (0.03 m) of 4-hydroxy-1-indanone in 50 ml of dimethylformamide is added 4.15 g (0.03 m) of potassium carbonate with stirring followed by the dropwise addition of 3.8 g (0.03 m) of benzyl chloride. The reaction mixture is heated at steam bath temperature for 3 hours, then cooled and diluted with water. The aqueous mixture is extracted with ethyl acetate and the extract is washed with water, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue is triturated with ether and concentrated to dryness to yield: 5.86 g (82%) of a brown solid, m.p. 70°-73° C., sufficiently pure to be used in the next step.

Workup

  1. temperatureThe reaction mixture is heated at steam bath temperature for 3 hours
  2. temperaturecooled
  3. extractionThe aqueous mixture is extracted with ethyl acetate
  4. washthe extract is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness in vacuo
  7. customThe residue is triturated with ether
  8. concentrationconcentrated to dryness to yield: 5.86 g (82%) of a brown solid, m.p. 70°-73° C.

Sources & evidence

ORD record
ord-9f18b5c968a44018bdc8b358ce612c3e
Source dataset
uspto-grants-1984_02
Patent number
US04431647

Linked notes

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