4-(5-Bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid-ethyl ester → 4-(5-Bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid

HRID 2054933Notes

Reaction equation

HRID 2054933 reaction equation
C([O:3][C:4](=[O:20])[C:5](=[O:19])[CH2:6][C:7]([C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])([CH3:9])[CH3:8])C>CO.[OH-].[Na+]>[Br:16][C:14]1[CH:13]=[CH:12][C:11]([O:17][CH3:18])=[C:10]([C:7]([CH3:9])([CH3:8])[CH2:6][C:5](=[O:19])[C:4]([OH:20])=[O:3])[CH:15]=1

Participants

4

Reactant 1

HCID 692032244-(5-Bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid-ethyl ester

Product 1

HCID 219488674-(5-Bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-(5-Bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid-ethyl ester in 30 ml of methanol and 12 ml of 1 M sodium hydroxide solution are stirred for 1 hour at room temperature, and the methanol is distilled off. It is mixed with water and hexane, the water phase is acidified with dilute hydrochloric acid while being cooled with ice, and it is mixed with ethyl acetate. The ethyl acetate phase is washed with water, dried (Na2SO4) and concentrated by evaporation. After crystallization from hexane, 1.8 g of 4-(5-bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid is obtained. Flash point: 80° C.

Workup

  1. distillationthe methanol is distilled off
  2. additionIt is mixed with water and hexane
  3. temperaturewhile being cooled with ice, and it
  4. additionis mixed with ethyl acetate
  5. washThe ethyl acetate phase is washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation
  8. customAfter crystallization from hexane

Sources & evidence

ORD record
ord-266b4f04dcee458b82113b082262a062
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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