Water → 1H-Benz[e]inden-1-ol, 2,3-dihydro-2-methyl-

HRID 1586275Notes

Reaction equation

HRID 1586275 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]1[C:12](=[O:13])[C:11]2[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]=[CH:7][C:6]=2[CH2:5]1.O>CO>[OH:13][CH:12]1[C:11]2[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]=[CH:7][C:6]=2[CH2:5][CH:4]1[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 108780732-Methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-one

Product 1

HCID 108888861H-Benz[e]inden-1-ol, 2,3-dihydro-2-methyl-Yield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (7.5 g) was added portion-wise at 0-20° C. to a solution of 18.1 g of 2,3-dihydro-2-methyl-benz[e]indene-1-one in 200 ml of methanol. The reaction was completed after 15 min of stirring, and the reaction mixture was poured into 400 ml of water. The organic layer was separated, and the water layer was extracted with diethyl ether. The combined organic layers were washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. The crude product was recrystallized from cyclohexane to obtain 14.3 g (78%) of 2,3-dihydro-1-hydroxy-2-methyl-1H-benz[e]indene.

Workup

  1. customThe organic layer was separated
  2. extractionthe water layer was extracted with diethyl ether
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe crude product was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-9376b8ad57c24c51b4d209c6711b23ae
Source dataset
uspto-grants-1999_08
Patent number
US05942636

Reaction notes

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