Benzyl Alcohol → Benzene, 1-nitro-4-(phenylmethoxy)-

HRID 365383Notes

Reaction equation

HRID 365383 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC.[H-].[Na+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>CS(C)=O>[CH2:1]([O:8][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8058HexaneHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydride

Product 1

HCID 70842Benzene, 1-nitro-4-(phenylmethoxy)-Yield 91.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
20 °C

Procedure

Benzyl alcohol (2.22 g, 20 mmol) was added to a slurry of hexane-washed NaH (60% oil suspension, 820 mg, 20.5 mmol) in DMSO (20 mL), stirred under nitrogen at 20° C., producing strong gas evolution. After 30 minutes, 1-fluoro-4-nitrobenzene (2.826 g, 20 mmol) was added dropwise to the light grey slurry. The reaction mixture became a bright orange red and quite strongly exothermic, and a lot of gas was evolved. After 2 hours, the reaction mixture was poured onto ice-water (200 mL), and the solid was collected by Buchner filtration, rinsed with water (2×50 mL), and air dried to give 1-benzyloxy-4-nitrobenzene (4.188 g, 91.3%) as canary yellow crystals. 1H NMR (DMSO-d6): δ8.16 (2 H, AA'BB', J=9.3 Hz), 7.47 (2 H, d, J=7.1 Hz), 7.41 (2 H, t, J=7.3 Hz), 7.36 (1 H, t, J=7.1 Hz), 7.23 (2 H, AA'BB', J=9.1 Hz), 5.26 (2 H, s).

Workup

  1. customproducing strong gas evolution
  2. waitAfter 2 hours
  3. additionthe reaction mixture was poured onto ice-water (200 mL)
  4. filtrationthe solid was collected by Buchner filtration
  5. washrinsed with water (2×50 mL), and air
  6. customdried

Sources & evidence

ORD record
ord-77453fba8fef47d49dd178accd1cab0c
Source dataset
uspto-grants-2000_10
Patent number
US06127374

Reaction notes

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