Dimethylformamide → 1-Benzyloxy-2-methoxymethyl-4-nitrobenzene

HRID 268551Notes

Reaction equation

HRID 268551 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[CH2:25]([O:13][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[CH2:3][O:2][CH3:1])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 113558782-(Methoxymethyl)-4-nitrophenol

Product 1

HCID 231042781-Benzyloxy-2-methoxymethyl-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18.3 g of 2-methoxymethyl-4-nitrophenol (1) (0.1 mol), 8.3 g (0.06 mol) of potassium carbonate and 40 ml of dimethylformamide were heated on a boiling water bath, and 12.1 ml (0.105 mol) of benzyl chloride were added over 10 minutes. After heating for 1 hour on the boiling water bath, the mixture was poured onto 150 g of ice. The yellow-brown crystals formed were filtered off, reslurried in ice-cold water and washed with petroleum ether. The wet product was recrystallized from 75 ml of isopropanol to give, after drying, 21 g of expected product with a melting point of 108° C. The results of the elementary analyses were as follows:

Workup

  1. customThe yellow-brown crystals formed
  2. filtrationwere filtered off
  3. washwashed with petroleum ether
  4. customThe wet product was recrystallized from 75 ml of isopropanol
  5. customto give
  6. customafter drying
  7. customThe results of the elementary analyses

Sources & evidence

ORD record
ord-408456023cbd4d0da593346be170b96f
Source dataset
uspto-grants-2008_11
Patent number
US07445645B2

Reaction notes

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