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

HRID 1110432Notes

Reaction equation

HRID 1110432 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-dec8f9896dba4ad08c77bf610d1e669f
Source dataset
uspto-grants-1990_12
Patent number
US04975456

Reaction notes

Loading…