Hydrochloric Acid → (4-(Benzyloxy)-3-nitrophenyl)methanol

HRID 1032512

Reaction equation

HRID 1032512 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>CO>[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 70235544-(Benzyloxy)-3-nitrobenzaldehyde

Product 1

HCID 13629301(4-(Benzyloxy)-3-nitrophenyl)methanolYield 79.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under ice cooling, 75.7 g of sodium borohydride is introduced within one hour into 128.0 g of 4-benzyloxy-3-nitrobenzaldehyde in 4.2 l of methanol. After 1.5 hours of agitation at room temperature, 1.1 l of 2N HCl is added dropwise. The isolated reaction product is recrystallized from a mixture of 680 ml of diisopropyl ether and 170 ml of isopropanol, thus obtaining 103.0 g of 4-benzyloxy-3-nitrobenzyl alcohol, mp 76°-77° C.

Workup

  1. customThe isolated reaction product
  2. customis recrystallized from a mixture of 680 ml of diisopropyl ether and 170 ml of isopropanol

Sources & evidence

ORD record
ord-332bfc4ec5674ccebc0f9df332c27bfd
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Linked notes

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