Pivalaldehyde → 2,2,4,4-Tetramethylpentan-3-ol

HRID 1906124Notes

Reaction equation

HRID 1906124 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH:3]=[O:4].[C:7]([Li])([CH3:10])([CH3:9])[CH3:8]>O1CCCC1>[C:2]([CH:3]([C:7]([CH3:10])([CH3:9])[CH3:8])[OH:4])([CH3:6])([CH3:5])[CH3:1]

Participants

4

Reactant 2

HCID 12417PivalaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 1397902,2,4,4-Tetramethylpentan-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trimethylacetaldehyde (5.12 g, 59.4 mmol) in anhydrous tetrahydrofuran (15 ml) at -78° C. under an argon atmosphere is added 40.9 ml of a solution of t-butyllithium in hexanes (1.6M, 65.4 mmol). The mixture is allowed to warm from -78° to room temperature over 2 hours. The reaction is quenched with 25 ml of 1M hydrochloric acid and the resulting mixture extracted with two 25 ml portions of ether. The combined ethereal extracts were washed with saturated sodium bicarbonate solution and water, dried over magnesium sulfate, and the solvent evaporated to yield a yellow oil (9.3 g) which is purified by vacuum distillation to yield a colorless oil.

Workup

  1. temperatureto warm from -78° to room temperature over 2 hours
  2. customThe reaction is quenched with 25 ml of 1M hydrochloric acid
  3. extractionthe resulting mixture extracted with two 25 ml portions of ether
  4. washThe combined ethereal extracts were washed with saturated sodium bicarbonate solution and water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-d65956726c3a4c85a72e05daacfd3500
Source dataset
uspto-grants-1987_03
Patent number
US04650688

Reaction notes

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