4'-Methoxyacetophenone → Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester

HRID 1955141Notes

Reaction equation

HRID 1955141 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[O:3].[C:12](=O)([O:16]CC)[O:13][CH2:14][CH3:15]>C1(C)C=CC=CC=1>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([CH2:1][C:12]([O:13][CH2:14][CH3:15])=[O:16])=[O:3])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 74764'-Methoxyacetophenone2×HCID 7766Diethyl Carbonate

Product 1

HCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
20 °C

Procedure

To potassium t-amylate (25 wt %, 50.8 kg, 99.26 mol) in toluene (15.2 kg) cooled to 5° C. under mechanical stirring and under nitrogen was added a mixture of 4-methoxyacetophenone (6.755 kg, 44.98 mol) and diethyl carbonate (6.40 kg, 54.18 mol) in toluene over 1 hour maintaining the temperature below 10° C. The reaction mixture was heated to 60° C. for 8 hours until no 4-methoxyacetophenone was detected by HPLC. The mixture was cooled to 20° C. and quenched by adding to a mixture of acetic acid (8 kg) and water (90 kg) over 30 minutes while maintaining the temperature at <20° C. The layers were separated, and the organic layer was washed with 5% sodium bicarbonate solution (41 kg) and concentrated to 14.65 kg. The temperature is maintained below 50° C. during the distillation. The yellow product concentrate was assayed by HPLC against an external standard and the yield was found to be 9.40 kg (94%).

Workup

  1. additionwas added
  2. temperaturemaintaining the temperature below 10° C
  3. customquenched
  4. additionby adding to a mixture of acetic acid (8 kg) and water (90 kg) over 30 minutes
  5. temperaturewhile maintaining the temperature at <20° C
  6. customThe layers were separated
  7. washthe organic layer was washed with 5% sodium bicarbonate solution (41 kg)
  8. concentrationconcentrated to 14.65 kg
  9. temperatureThe temperature is maintained below 50° C. during the distillation
  10. concentrationThe yellow product concentrate

Sources & evidence

ORD record
ord-5cc0b91cb6184bee9d51734c93bedf6f
Source dataset
uspto-grants-2000_09
Patent number
US06124341

Reaction notes

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