Sodium borohydride → HCID 66978202, compound

HRID 655104Notes

Reaction equation

HRID 655104 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-c37e9a41e2ab4fb5b322b202d6aa49c9
Source dataset
uspto-grants-2011_12
Patent number
US08071529B1

Reaction notes

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