Sodium borohydride → (3,4-Dimethoxy-5-propylphenyl)methanol

HRID 1381603Notes

Reaction equation

HRID 1381603 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH2:13][CH2:14][CH3:15])[C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[BH4-].[Na+]>CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[C:9]([CH2:13][CH2:14][CH3:15])[C:10]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 198382273,4-Dimethoxy-5-propylbenzaldehyde

Product 1

HCID 19838159(3,4-Dimethoxy-5-propylphenyl)methanolYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 3,4-dimethoxy-5-propylbenzaldehyde (11 g) and sodium borohydride (2 g) in 2-propanol (100 ml) was stirred at room temperature for 2 hours. The mixture was quenched with 2N HCl (200 ml) and extracted with ethyl acetate. The organic phase was separated, washed with brine, dried over MgSO4, filtered and evaporated to leave a yellow oil which was purified by Kugelrohr bulb to bulb distillation at 1 mm Hg air bath temperature 150° to give the sub-title compound as a colourless oil (8 g).

Workup

  1. customThe mixture was quenched with 2N HCl (200 ml)
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a yellow oil which
  9. distillationwas purified by Kugelrohr bulb to bulb distillation at 1 mm Hg air bath temperature 150°

Sources & evidence

ORD record
ord-37b5190365534e609a44ea5a2dadd234
Source dataset
uspto-grants-1989_02
Patent number
US04803225

Reaction notes

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