Sodium borohydride → HCID 66978202, compound

HRID 1807336Notes

Reaction equation

HRID 1807336 reaction equation
[CH3:1][C:2]12[CH2:9][CH:6]([CH2:7][CH2:8]1)[CH:5]([CH3:10])[C:4](=[O:11])[CH2:3]2.[BH4-].[Na+]>C(O)(C)C>[CH3:1][C:2]12[CH2:9][CH:6]([CH2:7][CH2:8]1)[CH:5]([CH3:10])[CH:4]([OH:11])[CH2:3]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66974043HCID 66974043, compound

Product 1

HCID 66978202HCID 66978202, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1,4-Dimethyl-bicyclo[3.2.1]octan-3-one (260 g, 1.7 mol, obtained as above in EXAMPLE III) was added to a suspension of sodium borohydride (NaBH4, 19 g, 0.5 mol) in isopropanol ((CH3)2CHOH, 400 mL), and refluxed for 30 minutes. The reaction mixture was cooled to room temperature, and quenched with acetone ((CH3)2CO) followed by acetic acid. The organic layer was separated and concentrated to provide crude 1,4-dimethyl-bicyclo[3.2.1]octan-3-ol (250 g, 1.6 mol), which was then added to a solution of acetic anhydride ((CH3CO)2O, 192 g, 1.9 mol) and Na2CO3 (4 g, 0.036 mol) and aged at 60° C. for 6 hours. The reaction mixture was subsequently washed with water followed by a Na2CO3 solution. Fractional distillation of the organic layer provided acetic acid 1,4-dimethyl-bicyclo[3.2.1]oct-3-yl ester (159 g) having a boiling point of 88° C. at a pressure of 15 mmHg.

Workup

  1. temperaturerefluxed for 30 minutes
  2. customquenched with acetone ((CH3)2CO)
  3. customThe organic layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-93861334b80e4aeb80179dd21f7dfc35
Source dataset
uspto-grants-2013_01
Patent number
US08357357B2

Reaction notes

Loading…