Acetic Acid → HCID 178458817, compound

HRID 1980793Notes

Reaction equation

HRID 1980793 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(O)(=O)C.C(OC(=O)C)(=O)C.[OH:16][C:17]1[CH2:22][CH:21]([C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)[CH2:20][C:19](=[O:32])[C:18]=1[C:33](=[O:36])[CH2:34][CH3:35]>O>[OH:32][C:19]1[CH2:20][CH:21]([C:23]2[CH:24]=[C:25]3[O:31][CH2:30][O:29][C:26]3=[CH:27][C:28]=2[N+:1]([O-:4])=[O:2])[CH2:22][C:17](=[O:16])[C:18]=1[C:33](=[O:36])[CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 7918Acetic Anhydride3×HCID 178458826HCID 178458826, compound

Product 1

HCID 178458817HCID 178458817, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution consisting of fuming nitric acid (0.84 g), glacial acetic acid (0.54 g) and acetic anhydride (0.54 g) was added to a mixture of 3-hydroxy-5-(3,4-methylenedioxyphenyl)-2-propionylcyclohex-2-en-1-one (2.60 g) and acetic anhydride (1.62 g) at 0° C. The mixture was stirred at 0°-3° C. for 1.5 hours with addition of extra portions of acetic anhydride when necessary to aid the stirring. The mixture was poured into water and the precipitate was collected and dried giving 3-hydroxy-5-(2-nitro-4,5-methylenedioxyphenyl)-2-propionylcyclohex-2-en-1-one as a yellow solid, mp 139° C.

Workup

  1. customthe precipitate was collected
  2. customdried

Sources & evidence

ORD record
ord-b1300c0fe7c74003a2178cd9b9162c86
Source dataset
uspto-grants-1985_04
Patent number
US04511391

Reaction notes

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