Acetic Acid → 5-Hydroxy-4,4-dimethylpentanoic acid

HRID 217231Notes

Reaction equation

HRID 217231 reaction equation
C[O:2][C:3](=O)[C:4]([CH3:11])([CH3:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8].CC(O)=O.O>C1COCC1>[OH:2][CH2:3][C:4]([CH3:11])([CH3:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 134932415-Methoxy-4,4-dimethyl-5-oxopentanoic acid

Product 1

HCID 542561495-Hydroxy-4,4-dimethylpentanoic acidYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

To a suspension of 2,2-dimethyl-pentanedioic acid 1-methyl ester (1.00 g, 5.75 mmol) in THF (3 mL), 1M LiBHEt3 in THF (38.0 ml, 38.0 mmol) is added dropwise maintaining the temperature below 10° C. under nitrogen. The mixture is stirred at 10° C. for 1 hour. To the mixture, 50% AcOH (4.6 mL) and H2O are added. The solution is extracted with AcOEt, and the organic layer is washed with H2O, dried over MgSO4, and concentrated under reduced pressure to give 5-hydroxy-4,4-dimethyl-pentanoic acid (850 mg, quant.); 1H NMR (400 MHz, chloroform-d) ppm 1.06 (s, 6H), 1.70 (t, 2H), 2.56 (t, 2H), 3.98 (s, 2H).

Workup

  1. additionis added dropwise
  2. temperaturemaintaining the temperature below 10° C. under nitrogen
  3. extractionThe solution is extracted with AcOEt
  4. washthe organic layer is washed with H2O
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d7d34d0e561244f6aa7f37732654dd12
Source dataset
uspto-grants-2012_06
Patent number
US08193349B2

Reaction notes

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