Water → 3,6-Dimethyl-2,4-heptanediol

HRID 132739Notes

Reaction equation

HRID 132739 reaction equation
[BH4-].[Na+].[OH-].[Na+].O.[CH3:6][CH:7]([C:11](=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:8](=[O:10])[CH3:9]>CO>[CH3:6][CH:7]([CH:11]([OH:16])[CH2:12][CH:13]([CH3:15])[CH3:14])[CH:8]([OH:10])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5382833,6-Dimethylheptane-2,4-dioneHCID 4311764Sodium borohydride

Product 1

HCID 671601493,6-Dimethyl-2,4-heptanediolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the mixture of 2.5 g sodium borohydride, 0.05 g sodium hydroxide, and 25 ml water was added dropwise the mixture of 14.2 g 3,6-dimethyl-2,4-heptandione and 30 ml methanol at 0-10° C. Upon completing the addition, the solvent was removed by reduced pressure distillation. The reaction mixture was continuously extracted with 40 ml ethyl acetate for 15 hours. The solvent was removed. Distillation under reduced pressure gave colorless liquid 3,6-dimethyl-2,4-heptanediol, and the yield was 90%. IR spectrum had a strong absorption peak at 3400 cm−1, and had no absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely.

Workup

  1. additionwas added dropwise
  2. additionthe addition
  3. customthe solvent was removed by reduced pressure distillation
  4. extractionThe reaction mixture was continuously extracted with 40 ml ethyl acetate for 15 hours
  5. customThe solvent was removed
  6. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-d687d064df1b462b9f2cce4640fe904f
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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