Hydrochloric Acid → 3,3-Dimethylpentane-1,5-diol

HRID 2065412Notes

Reaction equation

HRID 2065412 reaction equation
[CH3:1][C:2]([CH3:11])([CH2:7][C:8](O)=[O:9])[CH2:3][C:4](O)=[O:5].B.C1COCC1.Cl>O1CCCC1>[CH3:1][C:2]([CH3:11])([CH2:7][CH2:8][OH:9])[CH2:3][CH2:4][OH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 209843,3-Dimethylglutaric acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 128107743,3-Dimethylpentane-1,5-diolYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3,3-dimethylglutaric acid (Aldrich) (5.1 g, 32 mmol) in anhydrous tetrahydrofuran (100 mL) at 0° C. was added a solution of BH3.THF (1 M, 100 mL, 100 mmol). The reaction mixture was stirred at room temperature for 18 h. Aqueous HCl solution was added, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc) to give 3,3-dimethyl-pentane-1,5-diol as a colorless oil (1.5 g, 34%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc)

Sources & evidence

ORD record
ord-38b0355247da4008b0ba1b08658fc313
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

Loading…