Nitric Acid → HCID 19087769, compound

HRID 1464373Notes

Reaction equation

HRID 1464373 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[N+:18]([O-])([OH:20])=[O:19].O>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([O:11][CH3:12])=[O:10])=[CH:6][C:7]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962Water2×HCID 14674859HCID 14674859, compound

Product 1

HCID 19087769HCID 19087769, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

22.9 g (0.1 mol) of methyl 2-(4-hydroxyphenyl)-2-cyclopentyl-acetate are dissolved in 50 ml of CH2Cl2 and added dropwise at 5° C. to a solution of 50 ml of conc. HNO3 /50 ml of H2O. The mixture is stirred for 15 min, then 100 ml of H2O are added and the organic phase is separated off. The aqueous phase is extracted three times with 50 ml of CH2Cl2, and the organic phases are washed 5 times with water, dried, concentrated to a small volume and filtered through silica gel. After concentration, the product is obtained in 71% yield (20 g). The product is further processed in crude form.

Workup

  1. customthe organic phase is separated off
  2. extractionThe aqueous phase is extracted three times with 50 ml of CH2Cl2
  3. washthe organic phases are washed 5 times with water
  4. customdried
  5. concentrationconcentrated to a small volume
  6. filtrationfiltered through silica gel
  7. concentrationAfter concentration
  8. customthe product is obtained in 71% yield (20 g)

Sources & evidence

ORD record
ord-5396b3e855874f9b933a71dc4beba249
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

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