Nitric Acid → HCID 68734856, compound

HRID 1183582Notes

Reaction equation

HRID 1183582 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]([O:12]CC)=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[N+:19]([O-])([OH:21])=[O:20]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]([OH:12])=[O:11])[CH:5]=[C:6]([N+:19]([O-:21])=[O:20])[C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 57995575HCID 57995575, compound

Product 1

HCID 68734856HCID 68734856, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 2-(3-bromo-4-hydroxyphenyl)-4-methylpentanoate (16 g) was taken in acetic acid (100 ml) and to it added drop wise 70% nitric acid (10 ml) below 15° C. The reaction mixture was stirred for 2 h. After completion of the reaction; it was poured into 300 ml of ice water and extracted with ethyl acetate (300 ml×3). The ethyl acetate layer was washed with bicarbonate solution, water and finally brine solution. The organic layer was then distilled off and the crude residue was purified by column chromatography using Ethyl acetate:hexane (2:3) as eluent provided 12 g of 2-(3-bromo-4-hydroxy-5-nitrophenyl)-4-methylpentanoic acid. The acid was taken in 50 ml of absolute ethanol and 2 ml of concentrated sulfuric acid and refluxed for 1 h. The ethanol layer was distilled off, washed it with water and dried gave 13 g of ethyl 2-(3-bromo-4-hydroxy-5-nitrophenyl)-4-methylpentanoate intermediate. 1H NMR (CDCl3): δ 8.20 (s 1H), 7.20 (s, 1H), 4.90 (bs, 1H), 4.15 (q, 2H), 3.60 (t, 1H), 1.95-2.00 (m, 1H), 1.75-1.80 (m, 1H), 1.45-1.50 (m, 1H), 1.20 (t, 3H), 1.00 (m, 6H). Mass: (360, M+1,100%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (300 ml×3)
  3. washThe ethyl acetate layer was washed with bicarbonate solution, water and finally brine solution
  4. distillationThe organic layer was then distilled off
  5. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-bda4758986c041f4afde6bb07ef4c9ec
Source dataset
uspto-grants-2014_03
Patent number
US08664249B2

Reaction notes

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