Potassium Carbonate → 2,2-Dimethyl-5-[2,3,5-trimethyl-4-(phenylmethoxy) phenoxy]pentanoic acid, methyl ester

HRID 374286Notes

Reaction equation

HRID 374286 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([CH3:17])=[CH:4][C:3]=1[OH:18].Br[CH2:20][CH2:21][CH2:22][C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:28][C:23]([CH3:29])([CH2:22][CH2:21][CH2:20][O:18][C:3]1[CH:4]=[C:5]([CH3:17])[C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([CH3:8])[C:2]=1[CH3:1])[C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4303797Phenol, 2,3,5-trimethyl-4-(phenylmethoxy)-HCID 13050502Methyl 5-bromo-2,2-dimethylpentanoate

Product 1

HCID 1317176552,2-Dimethyl-5-[2,3,5-trimethyl-4-(phenylmethoxy) phenoxy]pentanoic acid, methyl esterYield 1,007.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 2-1, 3 neck, round bottom flask equipped with an overhead stirrer is charged with 29.4 g (12mmol) of 2,3,5-trimethyl-4-(phenylmethoxy)phenol (Example C), 29.8 g (1.1×12.1 mmol) of 5-bromo-2,2-dimethylvaleric acid, methyl ester (U.S. Pat. No. 4,665,226), 20.1 g (1.2×121 mmol) of anhydrous potassium carbonate and 300 mL of acetonitrile. The heterogeneous mixture is stirred at reflux for 96 hours. The solid is removed and the reaction flask and filtered solids are washed with fresh acetonitrile, the solvent removed and the residue taken up in 500 mL of hexane. On standing the product crystallizes partially and a seed crystal is retained. The solution is diluted to 700 mL with hexane and warmed to dissolve the product. After washing with 2×75 mL of 2N potassium hydroxide solution, and brine the solution is dried and evaporated leaving 46.5 g of a pale yellow solid. This crystallizes from 500 mL of hexane in the presence of charcoal and the solution is cooled to 0° C. and seeded to afford 41.4 g of the title compound as a colorless solid; mp 67°-68° C.

Workup

  1. customA 2-1, 3 neck, round bottom flask equipped with an overhead stirrer
  2. temperatureat reflux for 96 hours
  3. customThe solid is removed
  4. filtrationthe reaction flask and filtered solids
  5. washare washed with fresh acetonitrile
  6. customthe solvent removed
  7. customcrystallizes partially
  8. additionThe solution is diluted to 700 mL with hexane
  9. temperaturewarmed
  10. dissolutionto dissolve the product
  11. washAfter washing with 2×75 mL of 2N potassium hydroxide solution, and brine the solution
  12. customis dried
  13. customevaporated

Sources & evidence

ORD record
ord-031eed5e53bc43f6a24e25d0c930102e
Source dataset
uspto-grants-1992_11
Patent number
US05166398

Reaction notes

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