Potassium Hydroxide → HCID 57624623, compound

HRID 1641539Notes

Reaction equation

HRID 1641539 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([CH3:21])([C:16]([O:18]CC)=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH3:21])[C:16]([OH:18])=[O:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57624603Diethyl 2-[2-(4-bromophenyl)ethyl]-2-methylmalonate

Product 1

HCID 57624623HCID 57624623, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of diethyl 2-[2-(4-bromophenyl)ethyl]-2-methylmalonate (55.0 g) of Reference Example 24 in ethanol (300 mL) was added potassium hydroxide (85%, 12.2 g), and the mixture was stirred at 60° C. for 5 hr. The solvent was evaporated under reduced pressure, water was added, and the aqueous layer was washed with ether. The aqueous layer was acidified with hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (50.8 g) as a colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure, water
  2. additionwas added
  3. washthe aqueous layer was washed with ether
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7a57a3c886eb4a9eb750b174456b1f1c
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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