4-Hydroxybenzaldehyde → 4-(4-Nitrophenoxy)benzaldehyde

HRID 2119137Notes

Reaction equation

HRID 2119137 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.O>CN(C=O)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydride2×

Product 1

HCID 47395914-(4-Nitrophenoxy)benzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 61 g (0.5 mole) of 4-hydroxybenzaldehyde in 20 mL of dry DMF was added to a suspension of 0.5 mole of sodium hydride (from 24 g of 50% sodium hydride washed free of oil with hexane) in 500 mL of DMF. When the sodium hydride had completely dissolved, a solution of 53 mL (0.55 mole) of 4-fluoronitrobenzene was added and the reaction mixture was heated to 70°-80° C. for 2 hr. The mixture was then poured into water, the solid collected and recrystallized from iso-propanol. The solid was recrystallized again from ethanol to give 88 g (85% yield) of the title compound as a yellow solid, mp=101°-104° C.

Workup

  1. temperaturethe reaction mixture was heated to 70°-80° C. for 2 hr
  2. customthe solid collected
  3. customrecrystallized from iso-propanol
  4. customThe solid was recrystallized again from ethanol

Sources & evidence

ORD record
ord-7e7775eb54904beeb932eebacc4da3d2
Source dataset
uspto-grants-1987_07
Patent number
US04683239

Reaction notes

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