Water → (+/-)-1-(3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-ethanol

HRID 523343Notes

Reaction equation

HRID 523343 reaction equation
[CH3:1][C:2]1[C:3]([C:17](=[O:19])[CH3:18])=[CH:4][C:5]2[C:6]([CH3:16])([CH3:15])[CH2:7][CH:8]([CH3:14])[C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>CCOCC>[CH3:1][C:2]1[C:3]([CH:17]([OH:19])[CH3:18])=[CH:4][C:5]2[C:6]([CH3:16])([CH3:15])[CH2:7][CH:8]([CH3:14])[C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 89440TonalideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 89600820(+/-)-1-(3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-ethanolYield 101.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (±)-1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-ethanone (10.00 g, 38.7 mmol) in ether (65 ml) was added dropwise during 1 h to a suspension of LiAlH4 (1.48 g, 39.0 mmol) in ether (70 ml) at 0° C. The reaction mixture was left warming up to room temperature and then heated to reflux for 1 day. After cooling to 0° C. more LiAlH4 (0.76 g, 19.5 mmol) was added. After refluxing for another 3 days, the mixture was cooled to 0° C. and water was added dropwise. Extraction of the organic phase with water, drying over Na2SO4 and concentrating gave 10.19 g (99%) of the product.

Workup

  1. waitThe reaction mixture was left
  2. temperatureheated
  3. temperatureto reflux for 1 day
  4. additionwas added
  5. temperatureAfter refluxing for another 3 days
  6. temperaturethe mixture was cooled to 0° C.
  7. extractionExtraction of the organic phase with water
  8. dry with materialdrying over Na2SO4
  9. concentrationconcentrating

Sources & evidence

ORD record
ord-218c1398bdb54ffc899dc48949dade02
Source dataset
uspto-grants-2016_05
Patent number
US09334464B2

Reaction notes

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