Water → (2-Chloro-3-methoxy-4-nitrophenyl)methanol

HRID 2279867Notes

Reaction equation

HRID 2279867 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].O>CO>[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 866978032-Chloro-3-methoxy-4-nitrobenzaldehyde2×

Product 1

HCID 67812311(2-Chloro-3-methoxy-4-nitrophenyl)methanolYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-3-methoxy-4-nitrobenzaldehyde (Compound 54I, 1.6 g, 7.44 mmol) in methanol (25 mL) at 0° C. was added sodium borohydride (330 mg, 8.91 mmol). After stirring for 1.5 h, water (15 mL) was added. The solid obtained was filtered and dried to obtain the desired intermediate (1.1 g, 69%). 1H NMR (300 MHz, CDCl3) δ 7.78 (d, J=4.8 Hz, 1H), 7.47 (d, J=5.1 Hz, 1H), 4.83 (d, J=3.6 Hz, 2H), 4.02 (s, 3H), 2.25 (t, J=3.6 Hz, 1H).

Workup

  1. customThe solid obtained
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-db2b7274f3f74548aa3e0f9373d5c7a6
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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