t-Butyl bromide → 2,2,4,4-Tetramethylpentan-3-ol

HRID 1906359Notes

Reaction equation

HRID 1906359 reaction equation
[C:1](Br)([CH3:4])([CH3:3])[CH3:2].[Mg].[CH3:7][C:8]([CH3:12])([CH3:11])[CH:9]=[O:10]>CCOCC>[C:8]([CH:9]([OH:10])[C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:12])([CH3:11])[CH3:7]

Participants

5

Reactant 3

HCID 10485t-Butyl bromideHCID 12417PivalaldehydeHCID 5462224Magnesium2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of t-butyl bromide in ether is added slowly to magnesium stirrings until the Grignard reagent begins to form. The remainder of the alkyl bromide is then added and the mixture is stirred until all the magnesium dissolves. At 0° C., a solution of 2,2-dimethylpropionaldehyde is added and the resulting product is quenched with 1M HCl and extracted with ether and the solvent is evaporated to afford di-t-butylmethyl alcohol.

Workup

  1. customto form
  2. dissolutiondissolves
  3. customthe resulting product is quenched with 1M HCl
  4. extractionextracted with ether
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-7023021dbc684064a563dcb6abddc484
Source dataset
uspto-grants-1987_03
Patent number
US04652457

Reaction notes

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