Nitric Acid → HCID 13535751, compound

HRID 1583504Notes

Reaction equation

HRID 1583504 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].C(OC(=O)C)(=O)C.O[C@@H:13]1[CH2:17][C:16](=[O:18])[C:15]([CH2:19][CH:20]=[CH2:21])=[C:14]1[CH3:22]>C(Cl)(Cl)Cl>[CH3:22][C:14]1[C@H:13]([O:2][N+:1]([O-:4])=[O:3])[CH2:17][C:16](=[O:18])[C:15]=1[CH2:19][CH:20]=[CH2:21]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 12225759(4R)-4-Hydroxy-3-methyl-2-(prop-2-en-1-yl)cyclopent-2-en-1-one

Product 1

HCID 13535751HCID 13535751, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into a mixed solution of 8 g of fuming nitric acid and 24 g of acetic anhydride, kept at a temperature of -5° to 10° C. was added dropwise 6 g of (R)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one ([α]D24 : -7.81° (C=1.07, in chloroform), (R)-isomer/(S)-isomer=77.4/22.6). Thereafter, with the same operations as in Example 1, 7.50 g of crude (R)-3-methyl-4-nitroxy-2-(2-propenyl)-2-cyclopenten-1-one was obtained.

Workup

  1. customkept at a temperature of -5° to 10° C.

Sources & evidence

ORD record
ord-47594a5fed934e4f99d64cc4a3f435ca
Source dataset
uspto-grants-1985_11
Patent number
US04552703

Reaction notes

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