4,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxaldehyde → 4,6,6-Trimethyl-1,3-cyclohexadiene-1-methanol

HRID 566853Notes

Reaction equation

HRID 566853 reaction equation
[CH3:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[C:5]([CH:10]=[O:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[CH3:1][C:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[C:5]([CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 109206834,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 212637434,6,6-Trimethyl-1,3-cyclohexadiene-1-methanolYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 20 g (133 mole) of 4,6,6-trimethyl-1,3-cyclohexadiene-1-carbaldehyde in 100 ml of diethylether was added to a suspension of 1.5 g (39 mmole) of LiAlH4 in diethylether, under stirring and cooling with an ice-bath. After 1 h of reaction time, the mixture was hydrolyzed, the organic layer was separated, washed and dried and concentrated. The crude product was then distilled in vacuo, b.p. 60°/20 hPa, to obtain 11.6 g (56%) of the desired product.

Workup

  1. temperaturecooling with an ice-bath
  2. customAfter 1 h of reaction time
  3. customthe organic layer was separated
  4. washwashed
  5. customdried
  6. concentrationconcentrated
  7. distillationThe crude product was then distilled in vacuo, b.p. 60°/20 hPa

Sources & evidence

ORD record
ord-5ac3980826f6428d87d831b586e1b8ca
Source dataset
uspto-grants-2001_01
Patent number
US06177400B1

Reaction notes

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