Water → 2,4-Dibenzyloxybenzyl Alcohol

HRID 981384Notes

Reaction equation

HRID 981384 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[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.[Na].O>CO>[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[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 962WaterHCID 18090802,4-Bis(benzyloxy)benzaldehydeHCID 5360545Sodium

Product 1

HCID 105677102,4-Dibenzyloxybenzyl AlcoholYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,4-Dibenzyloxybenzaldehyde [V] (20 g) was dissolved in methanol (700 ml) and then, thereto was added sodium boronhydride (3.6 g) and this was left to stand at room temperature (20° C.) for 1.5 hours. To the reaction mixture was added water (1.5 liter) and the resulting precipitate was collected by filtration and recrystallized from ethanol to obtain 2,4-dibenzyloxybenzyl alcohol [VI] (19.8 g, yield 98%). Melting point: 84°-85° C.

Workup

  1. waitthis was left
  2. customto stand at room temperature
  3. custom(20° C.)
  4. customfor 1.5 hours
  5. filtrationthe resulting precipitate was collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0b0474d1060844e798031de3275388c5
Source dataset
uspto-grants-1991_02
Patent number
US04990614

Reaction notes

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