Pivalaldehyde → 2,2-Dimethylhex-5-en-3-ol

HRID 1174314Notes

Reaction equation

HRID 1174314 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH:3]=[O:4].[CH2:7]([Mg]Br)[CH:8]=[CH2:9]>C(OCC)C>[CH3:1][C:2]([CH3:6])([CH:3]([OH:4])[CH2:9][CH:8]=[CH2:7])[CH3:5]

Participants

4

Reactant 2

HCID 12417PivalaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 1405562,2-Dimethylhex-5-en-3-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of trimethylacetaldehyde (10.2 mL, 90.9 mmol) in diethyl ether (200 mL) at 0° C. was treated with allylmagnesium bromide (100 mL, 1 M in ether), stirred at 0° C. for 1 hour, quenched with saturated ammonium chloride and extracted with diethyl ether. The organic phase was washed with brine and dried over Na2SO4, filtered and concentrated to give the title compound (11.6 g).

Workup

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b43ebccd1ac24905b74a717053e46356
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…