Water → 1-(Hydroxymethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 132987Notes

Reaction equation

HRID 132987 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13](OCC)=[O:14])[C:7]=2[CH2:6][CH2:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[K+]>O1CCCC1>[OH:14][CH2:13][C:12]1[C:7]2[CH2:6][CH2:5][C:4]3[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=3[CH:2]([OH:1])[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58646833ethyl 5-oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-1-carboxylate

Product 1

HCID 586468421-(Hydroxymethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-olYield 104.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

560 mg of ethyl 5-oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-1-carboxylate prepared in Example 1-b was dissolved in 20 ml dry tetrahydrofuran, and 120 mg of lithium aluminum hydride was added under ice-cooling, followed by stirring for 2 hours. To the reaction mixture were successively added 0.1 ml of water, 0.1 ml of 15% potassium hydroxide solution and 0.3 ml of water, followed by stirring at room temperature for 0.5 hour. The reaction mixture was filtered through Celite, washed with ethyl acetate, and the solvent was evaporated, to give 500 mg of the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 0.5 hour
  3. filtrationThe reaction mixture was filtered through Celite
  4. washwashed with ethyl acetate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1edc9cd2a3e24502a6ea0113a4b1c8ac
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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