Nitric Acid → HCID 21526435, compound

HRID 1659072Notes

Reaction equation

HRID 1659072 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[N+:22]([O-])([OH:24])=[O:23].O.[OH-].[Na+]>CCOCC>[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:12]([N+:22]([O-:24])=[O:23])[CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 944Nitric Acid2×HCID 962Water2×HCID 14798Sodium HydroxideHCID 21526310HCID 21526310, compound

Product 1

HCID 21526435HCID 21526435, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl α -hydroxy-γ-(4-cyclohexylphenyl)butyrate 0.066 mole is added to ice-cold concentrated sulfuric acid (18 ml.) and stirred with cooling for 5 minutes. Concentrated nitric acid (Sp. G. 1.51) (2.5 ml.) is added dropwise, maintaining the temperature between 30° and 40° by water cooling if necessary. After addition of the nitric acid is complete, the mixture is stirred for 1/2 hour, then poured into water. The mixture is made alkaline with sodium hydroxide, then ex-racted with ether. The ether extract is washed, dried over sodium sulfate, evaporated and the residue is fractionally distilled to obtain ethyl α-hydroxy-γ-(3-nitro-4-cyclohexylphenyl)butyrate.

Workup

  1. temperaturewith cooling for 5 minutes
  2. stirringthe mixture is stirred for 1/2 hour
  3. extractionThe ether extract
  4. washis washed
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. distillationthe residue is fractionally distilled

Sources & evidence

ORD record
ord-981e94f579fc468d89f5d04393199747
Source dataset
uspto-grants-1976_06
Patent number
US03966801

Reaction notes

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