HCID 20070998, compound → HCID 20071020, compound

HRID 981806Notes

Reaction equation

HRID 981806 reaction equation
[CH3:1][C:2]1([CH3:16])[C:8](=[O:9])[C:7]([CH3:11])([CH3:10])[CH2:6][C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH3:1][C:2]1([CH3:16])[CH:8]([OH:9])[C:7]([CH3:10])([CH3:11])[CH2:6][C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 20070998HCID 20070998, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20071020HCID 20071020, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.57 g of 5,6,8,9-tetrahydro-6,6,8,8-tetramethyl-7H-benzocycloheptene-7-one are dissolved in 50 ml of absolute diethyl ether and treated cautiously at 0° with 460 mg of lithium aluminum hydride. The cooling bath is removed and the mixture is stirred at room temperature for an additional 2 hours. Then, 1.2 g of sodium hydroxide, dissolved in a small amount of water, are added portionwise, whereupon the reaction mixture is stirred until a filterable precipitate has formed. After filtration and evaporation of the filtrate, there is obtained 6,7,8,9-tetrahydro-6,6,8,8-tetramethyl-5H -benzocycloheptene-7-ol as a crude product which melts at 66°-68° after recrystallization from petroleum ether (low-boiling).

Workup

  1. customThe cooling bath is removed
  2. dissolutionThen, 1.2 g of sodium hydroxide, dissolved in a small amount of water
  3. additionare added portionwise, whereupon the reaction mixture
  4. stirringis stirred until a filterable precipitate
  5. customhas formed
  6. filtrationAfter filtration and evaporation of the filtrate

Sources & evidence

ORD record
ord-28f823c8bb4f4d86b7d2a3561f386fdc
Source dataset
uspto-grants-1991_02
Patent number
US04992574

Reaction notes

Loading…