Toluene → (2,3-Dichloro-6-nitrophenyl)methanol

HRID 41351

Reaction equation

HRID 41351 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([N+:18]([O-:20])=[O:19])[C:10]=1[CH:11]=[O:12].[BH4-].[Na+]>CO>[Cl:8][C:9]1[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([N+:18]([O-:20])=[O:19])[C:10]=1[CH2:11][OH:12]

Participants

5

Reactant 3

HCID 1140TolueneHCID 4311764Sodium borohydrideHCID 112182712,3-Dichloro-6-nitrobenzaldehyde

Product 1

HCID 11160370(2,3-Dichloro-6-nitrophenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To form 2,3-dichloro-6-nitrobenzylalcohol (compound XX) from 2,3-dichloro-6-nitro benzaldehyde (compound XIX), compound XIX is preferably solubilized in a solvent or solvent mixture such as toluene and methanol. The solution of compound XIX is added to a reducing solution such as sodium borohydride in an organic solvent over a period of time to maintain a reaction temperature below about 40° C., preferably 25° C. The reaction is preferably stirred for 24 hours at room temperature under nitrogen and then washed with water. After removing the aqueous layer the organic layer is azeotropically dried and concentrated forming 2,3-dichloro-6-nitrobenzylalcohol (compound XX).

Workup

  1. washwashed with water
  2. customAfter removing the aqueous layer the organic layer
  3. customis azeotropically dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4b7498d6d4404f80b161caa37cf7fac8
Source dataset
uspto-grants-2013_09
Patent number
US08530651B2

Linked notes

Loading…