Sodium Hydroxide → HCID 19359190, compound

HRID 1417900Notes

Reaction equation

HRID 1417900 reaction equation
C([O:3][C:4](=[O:17])[CH:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=1)[CH2:6][CH3:7])C.[OH-].[Na+]>C(O)C.O>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([CH:5]([CH2:6][CH3:7])[C:4]([OH:17])=[O:3])=[CH:9][CH:10]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70061726HCID 70061726, compound

Product 1

HCID 19359190HCID 19359190, compoundYield 123.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-acetylphenylbutyric acid ethyl ester (50.0 g, 0.21 mol) in ethanol (1250 mL) was added, dropwise, a solution of sodium hydroxide (50.0 g) in water (1250 mL). All was stirred at reflux over 4 hours. The solution was concentrated to half volume and then acidified to a pH equal to 1.0 using hydrochloric acid (1N). The resulting precipitate was collected and washed with water to give 4-acetylphenylbutyric acid (53.76 g, 0.26 mol, 99%) as a white solid. mp=50°-52° C.; 1H NMR (CDCl3) d 7.9 (d, 2H, J=8.1 Hz), 7.25 (d, 2H, J=9.1 Hz), 2.75 (t, 2H, J=7.7 Hz), 2.6 (s, 3H), 2.4 (t, H, J=7.3 Hz), 2.0 (quintet, 2H, J=7.4 Hz).

Workup

  1. temperatureat reflux over 4 hours
  2. concentrationThe solution was concentrated to half volume
  3. customThe resulting precipitate was collected
  4. washwashed with water

Sources & evidence

ORD record
ord-851c50f4e58d4c6e826d2c6b3a699fc4
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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