Benzophenone → Isonitrosoacetophenone

HRID 1184318Notes

Reaction equation

HRID 1184318 reaction equation
CC(C)([O-])C.[K+].[C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])[C:8]1C=CC=CC=1.[N:21](OCCC(C)C)=[O:22]>C(O)(C)(C)C>[O:14]=[C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:8]=[N:21][OH:22]

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 8053Isoamyl NitriteHCID 23665647Potassium tert-butoxide

Product 1

HCID 6399018Isonitrosoacetophenone

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

A flask was charged with potassium tert-butoxide (58 mmol) and 63 mL of tert-butyl alcohol. The mixture was stirred until a solution was formed, and a solution of the appropriate benzophenone (50 mmol) in 35 mL of tert-butyl alcohol added dropwise over 15 min. The reaction mixture was stirred for 1 hr, and the neat isoamyl nitrite (75 mmol) added over five min. The reaction mixture was monitored for completion and then diluted with 100 mL of heptanes. The resulting solid (38 mmol) was collected via suction filtration and dried to a constant weight under vacuum. Procedure was adapted from: Hagedorn et al., Chem. Ber., 98:193 (1965).

Workup

  1. customwas formed
  2. stirringThe reaction mixture was stirred for 1 hr
  3. customdried to a constant weight under vacuum

Sources & evidence

ORD record
ord-f63d5a0605754100b5d423b1853aaaa4
Source dataset
uspto-grants-2014_03
Patent number
US08669103B2

Reaction notes

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