3-(allyloxy)benzaldehyde → {3-[(Prop-2-en-1-yl)oxy]phenyl}methanol

HRID 2395001Notes

Reaction equation

HRID 2395001 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])[CH:2]=[CH2:3].[BH4-].[Na+]>CO>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][OH:9])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 27166123-(allyloxy)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 28065595{3-[(Prop-2-en-1-yl)oxy]phenyl}methanolYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-allyloxybenzaldehyde (7.2 g) in methanol (50 ml) at 0° C. was added sodium borohydride (1 g) in portions. The mixture was stirred for 30 minutes, evaporated dissolved in 5% acetic acid and extracted with diethyl ether (3×100 ml) , washed with water (2×100 ml), and sodium bicarbonate (2×100 ml), dried (magnesium sulphate), filtered and evaporated to give 3-allyloxybenzyl alcohol (7.26 g).

Workup

  1. customevaporated
  2. dissolutiondissolved in 5% acetic acid
  3. extractionextracted with diethyl ether (3×100 ml)
  4. washwashed with water (2×100 ml), and sodium bicarbonate (2×100 ml)
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-10aaf8e3973b4bf69bbb04ed2863036c
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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