2-Nitrophenol → 2,2-Dimethyl-5-(3-nitrophenoxy)pentanoic acid, methyl ester

HRID 1639117Notes

Reaction equation

HRID 1639117 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1O)([O-:3])=[O:2].[CH3:11][O:12][C:13](=[O:21])[C:14]([CH3:20])([CH3:19])[CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-:23].[K+].[K+]>C(#N)C>[CH3:19][C:14]([CH3:20])([CH2:15][CH2:16][CH2:17][O:23][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:13]([O:12][CH3:11])=[O:21]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 13050502Methyl 5-bromo-2,2-dimethylpentanoate

Product 1

HCID 1317161982,2-Dimethyl-5-(3-nitrophenoxy)pentanoic acid, methyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 27.8 g (200 mmol) of 2-nitrophenol, 44.6 g (200 mmol) of methyl-5-bromo-2,2-dimethylpentanoate (Journal of Medicinal Chemistry, Vol. 26, pp 1020-1027 (1983)) and 30.5 g (220 mmol) of anhydrous potassium carbonate in 300 ml of acetonitrile is stirred at reflux for 18 hours. The inorganic salts are removed, washed with acetonitrile and the filtrate is concentrated on a rotary evaporator. The residue is taken up in diethyl ether and the solution washed with 2N potassium hydroxide (3×50 ml), brine, dried (magnesium sulfate), and evaporated to afford 55.9 g of crude product. Distillation gives 52.9 g of 2,2-dimethyl-5-(3-nitrophenoxy)pentanoic acid, methyl ester, bp 160°-165° C. (0.5 mm).

Workup

  1. temperatureat reflux for 18 hours
  2. customThe inorganic salts are removed
  3. washwashed with acetonitrile
  4. concentrationthe filtrate is concentrated on a rotary evaporator
  5. washthe solution washed with 2N potassium hydroxide (3×50 ml), brine
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated
  8. customto afford 55.9 g of crude product
  9. distillationDistillation

Sources & evidence

ORD record
ord-63caa96182ae41a3a76e7051a837d16e
Source dataset
uspto-grants-1989_11
Patent number
US04882357

Reaction notes

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