Water → 3,3-Dimethylheptan-2-one

HRID 1706039Notes

Reaction equation

HRID 1706039 reaction equation
[CH3:1][C:2]([CH3:10])([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([OH:5])=O.[CH3:11][Li].O>CCOCC>[CH3:10][C:2]([CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[C:3](=[O:5])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 1632172,2-Dimethylhexanoic AcidHCID 178418348HCID 178418348, compound

Product 1

HCID 127541953,3-Dimethylheptan-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 14.4 g (100 mmol) of 2,2-dimethylhexanoic acid (XXIX) in 100 ml of dry ether was stirred a 0° C. under argon as 130 ml (237 mol) of a solution of methyllithium (1.82 M) in ether was added dropwise. The resultant mixture was stirred with ice-bath cooling for 1 hour and then without cooling overnight. It was then poured into a vigorously stirred 500 ml portion of water in a large beaker. The phases were separated and the aqueous phase was back-extracted twice with ether. The combined extract was dried (MgSO4) and evaporated in vacuo. The residue was distilled at 20 mm to yield 12.7 g of XXX as a colorless oil, bp 125°-130°; Rf (CHCl3) 0.54; nmr 0.9 (3, broad t, J=6.0 Hz), 1.12 (6, s), 1.0-1.8 (6, m) and 2.14 (3, s); ir (film) 8.85, 7.45, 6.80, 5.85, 3.50, 3.41 and 3.38μ.

Workup

  1. additionwas added dropwise
  2. temperaturecooling for 1 hour
  3. temperaturewithout cooling overnight
  4. customThe phases were separated
  5. extractionthe aqueous phase was back-extracted twice with ether
  6. extractionThe combined extract
  7. dry with materialwas dried (MgSO4)
  8. customevaporated in vacuo
  9. distillationThe residue was distilled at 20 mm

Sources & evidence

ORD record
ord-da290f89a8a7429cafb0695fbbb0a650
Source dataset
uspto-grants-1980_06
Patent number
US04206127

Reaction notes

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