Hydride → 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthylmethanol

HRID 2294551Notes

Reaction equation

HRID 2294551 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:23])[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]2[CH:13]=[C:12]([C:20](O)=[O:21])[CH:11]=[CH:10][C:9]1=2.[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[CH3:7][C:8]1([CH3:23])[CH2:17][CH2:16][C:15]([CH3:18])([CH3:19])[C:14]2[CH:13]=[C:12]([CH2:20][OH:21])[CH:11]=[CH:10][C:9]1=2

Participants

6

Reactant 4

HCID 166653HydrideHCID 2276385,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acidHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 144256215,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.8 g (0.1 tool) of lithium aluminium hydride and 100 ml of THF are introduced into a round-bottomed flask. Under a stream of nitrogen, a solution of 11.6 g (0.05 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoic acid in 100 ml of THF is added dropwise and the mixture is heated to reflux for four hours. The excess hydride is hydrolyzed with 7.2 ml of a 10% solution of sodium potassium tartrate, the precipitate is filtered off and the organic phase is evaporated. 10.6 g (97%) of the expected alcohol, melting point 74°-75° C., are collected.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for four hours
  3. filtrationthe precipitate is filtered off
  4. customthe organic phase is evaporated
  5. custom10.6 g (97%) of the expected alcohol, melting point 74°-75° C., are collected

Sources & evidence

ORD record
ord-eb432eb017ce4cbbb69e5d178115510a
Source dataset
uspto-grants-1997_11
Patent number
US05688817

Reaction notes

Loading…