Potassium Carbonate → HCID 86746451, compound

HRID 1645884Notes

Reaction equation

HRID 1645884 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:12])[C:7]([OH:11])=[CH:8][C:9]=1[CH3:10])([O-:3])=[O:2].Br[CH2:14][CH2:15][CH2:16][C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:12][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:9]([CH3:10])=[CH:8][C:7]=1[O:11][CH2:14][CH2:15][CH2:16][C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2821102,5-Dimethyl-4-nitrophenolHCID 13050502Methyl 5-bromo-2,2-dimethylpentanoate

Product 1

HCID 86746451HCID 86746451, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 16.7 g (100 mmol) of 4-nitro-2,5-xylenol, 24.5 g (110 mmol) of 5-bromo-2,2-dimethylvaleric acid, methyl ester (U.S. Pat. No. 4,665,226) and 15.3 g (110 mmol) of anhydrous potassium carbonate in 200 mL of acetonitrile is stirred at reflux for 18 hours overnight. The inorganic solid is removed, washed thoroughly with fresh acetonitrile and the filtrate is evaporated. The solid residue is stirred with a mixture of diethyl ether and 100 mL of 2N potassium hydroxide solution. The aqueous layer is removed and the organic layer washed with 50 mL of 2N potassium hydroxide solution, brine, dried, and evaporated. The crystalline residue is taken up in hexane (hot), treated with charcoal to assist in removal of some insoluble material, concentrated to 200 mL, and cooled to afford 18.2 g of the title compound as pale yellow needles; mp 73°-75° C.

Workup

  1. temperatureat reflux for 18 hours overnight
  2. customThe inorganic solid is removed
  3. washwashed thoroughly with fresh acetonitrile
  4. customthe filtrate is evaporated
  5. customThe aqueous layer is removed
  6. washthe organic layer washed with 50 mL of 2N potassium hydroxide solution, brine
  7. customdried
  8. customevaporated
  9. additiontreated with charcoal
  10. customto assist in removal of some insoluble material
  11. concentrationconcentrated to 200 mL
  12. temperaturecooled

Sources & evidence

ORD record
ord-e032a7d372c042adb9401288cdcebdab
Source dataset
uspto-grants-1993_01
Patent number
US05177106

Reaction notes

Loading…