Water → 2-Chloro-3-benzyloxy-6-nitrotoluene

HRID 1898982Notes

Reaction equation

HRID 1898982 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[OH:12].[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[Cl:1][C:2]1[C:3]([O:12][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 131473552-Chloro-3-methyl-4-nitrophenol

Product 1

HCID 233730582-Chloro-3-benzyloxy-6-nitrotolueneYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-3-methyl-4-nitrophenol (30.0g, 0.160 mol) in sieve-dried DMF (650 ml) was treated with sodium hydride (50%, 8.44g, 0.176 mol) and then benzyl bromide (30.1 g, 0.176 mol), while stirring at 0° C. The mixture was stirred at room temperature for 16 hours, then poured into 3 litres of water to precipitate an orange-coloured solid, which was recrystallised from ethanol to give 2-chloro-3-benzyloxy-6-nitrotoluene (31.3 g) m.p. 73°-74.5° C.

Workup

  1. customto precipitate an orange-coloured solid, which
  2. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-264436ea6d934d9da8dff88e945d7637
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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