Methanol → 2-(Methoxymethyl)-4-nitrophenol

HRID 268550

Reaction equation

HRID 268550 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].[CH3:13][OH:14].C[O-].[Na+]>O>[CH3:13][O:14][CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 763052-(Chloromethyl)-4-nitrophenolHCID 10942334Sodium Methoxide

Product 1

HCID 113558782-(Methoxymethyl)-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18.7 g (0.1 mol) of 2-chloromethyl-4-nitrophenol and 50 ml of pure methanol were mixed together and refluxed for 2 hours 30 minutes. 37 ml of sodium methoxide (0.2 mol, 5.4 N solution in MeOH) were added and the mixture was refluxed for another 30 minutes. The resulting mixture was cooled in an ice bath and diluted with 350 ml of water, and the insoluble matter formed was filtered off. The filtrate was acidified with acetic acid (10 ml). The crystalline product was filtered off by suction, reslurried in ice-cold water and then dried over P2O5 at 40° C. 11.4 g of crude products were isolated and then recrystallized from 15 ml of isopropyl acetate to give 7.5 g of expected product.

Workup

  1. temperaturerefluxed for 2 hours 30 minutes
  2. temperaturethe mixture was refluxed for another 30 minutes
  3. temperatureThe resulting mixture was cooled in an ice bath
  4. customthe insoluble matter formed
  5. filtrationwas filtered off
  6. filtrationThe crystalline product was filtered off by suction
  7. dry with materialdried over P2O5 at 40° C
  8. custom11.4 g of crude products were isolated
  9. customrecrystallized from 15 ml of isopropyl acetate

Sources & evidence

ORD record
ord-0a0551b5bf3049c0a58006b54583054c
Source dataset
uspto-grants-2008_11
Patent number
US07445645B2

Linked notes

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