Reaction #355733

Reaction equation

benzyl chloride

2-methoxymethyl-4-nitrophenol

potassium carbonate

dimethylformamide

→

1-benzyloxy-2-methoxymethyl-4-nitrobenzene

Solvents

water

Conditions

Workup

1. 1
   OtherThe yellow-brown crystals formed
2. 2
   Filtrationwere filtered off
3. 3
   Washwashed with petroleum ether
4. 4
   OtherThe wet product was recrystallized from 75 ml of isopropanol
5. 5
   Otherto give
6. 6
   Otherafter drying
7. 7
   OtherThe results of the elementary analyses

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:

Source