Acetone → (2-(Benzyloxy)-3-methoxyphenyl)methanol

HRID 5901

Reaction equation

HRID 5901 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CC(C)=O>C(O)C>[CH2:1]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 12680872-(Benzyloxy)-3-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 927250(2-(Benzyloxy)-3-methoxyphenyl)methanolYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 43.00 g (0.18 mole) of 2-benzyloxy-3-methoxy-benzaldehyde of Example 1 in 300 mL of absolute ethanol is treated, with stirring, with 7.56 g (0.20 mole) of sodium borohydride. The temperature rises to 50° C. After one-half hour 10 mL of acetone is added, keeping the temperature at less than 60° C. with cooling. After 15 minutes the volatiles are stripped off at reduced pressure. Ice water (500 mL) is added and the product is extracted into 600 mL of ethyl acetate. The dried (Na2SO4) solution is concentrated. The remaining oil is dissolved in 100 mL of warm ether. Petroleum ether is added to turbidity to give 37.70 g (86% yield) of pure product; mp 58°-60° C.

Workup

  1. customrises to 50° C
  2. customat less than 60° C.
  3. temperaturewith cooling
  4. extractionthe product is extracted into 600 mL of ethyl acetate
  5. dry with materialThe dried (Na2SO4) solution
  6. concentrationis concentrated
  7. dissolutionThe remaining oil is dissolved in 100 mL of warm ether
  8. additionPetroleum ether is added to turbidity

Sources & evidence

ORD record
ord-27c222d747194cee97fae27c69eb7117
Source dataset
uspto-grants-1993_09
Patent number
US05246943

Linked notes

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