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Sulfuric Acid → 1-Phenylethyl Acetate

HRID 1885083
Notes
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Reaction equation

HRID 1885083 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2].N([O:11][C:12]([CH3:15])(C)C)=O.[OH:16]N1C(=O)C2=CC=CC=C2C1=O.S(=O)(=O)(O)O.[OH-].[Na+].C(=NO)(C1C=CC=CC=1)C.[N+](C(C1C=CC=CC=1)C)([O-])=O.C(C1C=CC=CC=1)(=O)C>C(O)(=O)C>[C:12]([O:11][CH:1]([CH3:2])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:16])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 8

HCID 1118Sulfuric AcidHCID 7410AcetophenoneHCID 7500EthylbenzeneHCID 10665N-HydroxyphthalimideHCID 10906Tert-Butyl nitriteHCID 14798Sodium HydroxideHCID 236181-Nitroethylbenzene
HCID 69185
Acetophenonoxime

Product 1

HCID 623411-Phenylethyl Acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Ethylbenzene (2 ml), t-butyl nitrite (4 mmol), N-hydroxyphthalimide (0.4 mmol), and acetic acid (2 ml) were placed in a flask and were stirred at 80° C. in an atmosphere of argon gas for 2.5 hours. The resulting mixture was further treated with sulfuric acid having a concentration of 98% by weight (200 mg) with stirring at 70° C. for 15 minutes. The reaction mixture was then neutralized with sodium hydroxide and was analyzed to find that acetophenone oxime, (1-nitroethyl)benzene, acetophenone, and α-methylbenzyl acetate were formed in yields of 61%, 1%, 8%, and 5%, respectively.

Workup

  1. stirringwith stirring at 70° C. for 15 minutes

Sources & evidence

ORD record
ord-f44d2a595cbf495c8f576e7c30ced97c
Source dataset
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06768023B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes