Water → Pivaloin

HRID 2367863Notes

Reaction equation

HRID 2367863 reaction equation
[OH-:1].[Na+].Br[CH:4]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:5](=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7].O>C(N(CC)C=O)C>[OH:1][CH:4]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:5](=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 12387514HCID 12387514, compound

Product 1

HCID 219593Pivaloin

Reagents, catalysts & solvents 1

HCID 12051DiethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

5 g (0.125 mol) of sodium hydroxide powder was added to 11.6 g (0.05 mol) of 4-Bromo-2,2,5,5-tetramethyl-3-hexanone in 10 g of dry diethylformamide. This reaction mixture was heated to 110° C. for 2 hours, cooled to room temperature and 600 mL of water and 200 mL of hexanes added. The hexane layer was collected and the aqueous layer was washed three times with 50 ml of additional hexanes. The hexanes fractions were then combined, washed three times with 50 ml water, then dried with MgSO4. The product was collected as a crystalline solid after hexanes removal by atmospheric distillation.

Workup

  1. temperaturecooled to room temperature
  2. customThe hexane layer was collected
  3. washthe aqueous layer was washed three times with 50 ml of additional hexanes
  4. washwashed three times with 50 ml water
  5. dry with materialdried with MgSO4
  6. customThe product was collected as a crystalline solid
  7. customafter hexanes removal
  8. distillationby atmospheric distillation

Sources & evidence

ORD record
ord-7eb41d6cf5a5401d96dfbf4d712ac80c
Source dataset
uspto-grants-2014_04
Patent number
US08703103B2

Reaction notes

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