Water → 6-Nitroveratryl alcohol

HRID 1632787Notes

Reaction equation

HRID 1632787 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:5]=1[CH:6]=[O:7])([O-:3])=[O:2].O.[BH4-].[Na+]>C(O)C>[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 885056-NitroveratraldehydeHCID 4311764Sodium borohydride

Product 1

HCID 660976-Nitroveratryl alcoholYield 56.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
40 °C

Procedure

1011 g of 2-nitro-4,5-dimethoxybenzaldehyde in 10 l of ethanol with 94.8 ml water added was stirred, and a solution of 57 g sodium borohydride in 2 l absolute ethanol was added over 1 hour. The mixture was heated to 40° C. for 2.5 hours, cooled to 5° C. and the mixture filtered. The solid was washed with 4 l of cold 2B alcohol (denatured ethanol) and 8 l cold water, and dried in a 50° C. vacuum oven to yield 570 g, 56.5% yield.

Workup

  1. temperaturecooled to 5° C.
  2. filtrationthe mixture filtered
  3. washThe solid was washed with 4 l of cold 2B alcohol (denatured ethanol) and 8 l cold water
  4. customdried in a 50° C. vacuum oven
  5. customto yield 570 g, 56.5% yield

Sources & evidence

ORD record
ord-5aa1cce3c7fd47829d585ffeb2af4841
Source dataset
uspto-grants-1984_10
Patent number
US04477556

Reaction notes

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