5H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo- → 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propan-1-ol

HRID 1658985Notes

Reaction equation

HRID 1658985 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]=[C:8]1[C:14]2[CH:15]=[CH:16][C:17]([CH:19]([CH3:23])[C:20](O)=[O:21])=[CH:18][C:13]=2[CH:12]=[CH:11][C:10]2[CH:24]=[CH:25][CH:26]=[CH:27][C:9]1=2>CCOCC>[O:7]=[C:8]1[C:14]2[CH:15]=[CH:16][C:17]([CH:19]([CH3:23])[CH2:20][OH:21])=[CH:18][C:13]=2[CH:12]=[CH:11][C:10]2[CH:24]=[CH:25][CH:26]=[CH:27][C:9]1=2

Participants

4

Reactant 2

HCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-HCID 21226445Aluminium lithium hydride

Product 1

HCID 214093932-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.5 G. of lithium aluminum hydride is added to a solution of 2.78 g. of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid in 200 ml. of anhydrous ether. The mixture is stirred for 2 hours and then excess hydride is destroyed by sequential addition of ethyl acetate, methanol and water. The ethereal solution is separated and filtered and to it is added 15 g. of activated manganese dioxide. The mixture is stirred for 8 hours, then filtered through 10 g. of silica gel and the eluate evaporated to afford 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propan-1-ol (m.p. 63°-66°C).

Workup

  1. customexcess hydride is destroyed by sequential addition of ethyl acetate, methanol and water
  2. customThe ethereal solution is separated
  3. filtrationfiltered and to it
  4. additionis added 15 g
  5. stirringThe mixture is stirred for 8 hours
  6. filtrationfiltered through 10 g
  7. customof silica gel and the eluate evaporated

Sources & evidence

ORD record
ord-38cbab290fe54bc3823873dc29a4a4f6
Source dataset
uspto-grants-1976_06
Patent number
US03966820

Reaction notes

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