Hydrochloric Acid → 4-(2-Methoxy-5-methylphenyl)-4-oxobutanoic acid

HRID 2290927Notes

Reaction equation

HRID 2290927 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7](=[O:17])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])C.Cl>[OH-].[Na+]>[O:17]=[C:7]([C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])[CH2:6][CH2:5][C:4]([OH:18])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20230698Ethyl 4-(2-methoxy-5-methylphenyl)-4-oxobutanoate

Product 1

HCID 2989124-(2-Methoxy-5-methylphenyl)-4-oxobutanoic acidYield 80.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl-4-keto-γ-(2-methoxy-5-methylphenyl)-butyrate (180 g, 0.81 mole) and 1200 mL 20% NaOH was stirred at reflux for 3 hours. After cooling to 0°, the solution was acidified with concentrated HCl. The solid was filtered, washed with water, dried (in-vacuo) to yield 145 g orange solid. Recrystallization from CCl4 yielded 123 g light yellow powder, (68%).

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling to 0°
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried (in-vacuo)

Sources & evidence

ORD record
ord-06ca8c6bf47243c4bc314b966f46a15f
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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