Ethylbenzene → 1-Phenylethanol

HRID 992148

Reaction equation

HRID 992148 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2].[OH:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2C1=O.[N]=[O:22]>C(O)(=O)C>[N+:10]([CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2])([O-:9])=[O:22].[OH:15][CH:14]([C:13]1[CH:12]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:1]

Participants

6

Reactant 3

HCID 7500Ethylbenzene2×HCID 10665N-HydroxyphthalimideHCID 145068Nitric Oxide

Product 2

HCID 74091-PhenylethanolYield 18%HCID 236181-NitroethylbenzeneYield 14%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a flask, 1 mmole of ethylbenzene, 0.05 mmole of N-hydroxyphthalimide and 5 ml of acetic acid were added to mix and the flask was equipped with a gas bag (about 1L)of nitrogen monoxide NO. The mixture was reacted for 8 hours at 100° C. with stirring. The reaction products were analyzed by gas chromatography, and, as a result, the conversion of ethylbenzene was 85%, and 1-nitroethylbenzene (yield 14%), 1-hydroxyethylbenzene (yield 18%) and 1-acetyloxyethylbenzene (yield 30%) were formed.

Workup

  1. additionto mix
  2. customThe mixture was reacted for 8 hours at 100° C.

Sources & evidence

ORD record
ord-c458f446724549468ddfe965d5681074
Source dataset
uspto-grants-2002_10
Patent number
US06468487B1

Linked notes

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