Acetic Acid → Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester

HRID 964178Notes

Reaction equation

HRID 964178 reaction equation
[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:11].C(O)(=O)C.C(C1C=CC=CC=1)(=O)C>C1(C)C=CC=CC=1.O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10](=[O:11])[CH2:9][C:1]([O:5][CH2:6][CH3:7])=[O:8])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7410AcetophenoneHCID 74764'-MethoxyacetophenoneHCID 7766Diethyl Carbonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent5×

Procedure

The mixture was agitated for 5 minutes and allowed to settle. 20 L of the toluene solution was aspirated. 28 L of toluene was added, agitated for 5 minutes, allowed to settle and 28 L of the toluene solution was aspirated. 68 L of toluene and 8.4 L (69.7 moles) diethyl carbonate were added. The agitation was begun and the flow of Syltherm (Note 4) in reactor jackets was initiated. A solution of 5.0 kg (33.3 moles) 4-methoxyacetophenone in 12 L toluene was added over 20 minutes. When additions were complete, the jacket temperaturewas reduced to 10° C. and stirring continued for 16 hours. A solution of 6.7 L (117 moles) glacial acetic acid in 23 L deionized water was fed at the same rate that was previously used for the acetophenone solution. When addition was complete, agitation was stopped and the layers separated. The aqueous layer was washed once with 13 L toluene. The combined organic layers were washed twice with 6.7 L portions of 7% (w:w) aqueous sodium bicarbonate. The toluene solution was washed once with 6.7 L of 23% (w:w) aqueous sodium chloride . The organinc solution was dried over 10 kg sodium sulfate, filtered, and the solvent removed on the rotary evaporator to provide the desired product.

Workup

  1. stirringagitated for 5 minutes
  2. customthe flow of Syltherm (Note 4) in reactor jackets was initiated
  3. customtemperaturewas reduced to 10° C.
  4. stirringstirring
  5. waitcontinued for 16 hours
  6. additionWhen addition
  7. customthe layers separated
  8. washThe aqueous layer was washed once with 13 L toluene
  9. washThe combined organic layers were washed twice with 6.7 L portions of 7% (w:w) aqueous sodium bicarbonate
  10. washThe toluene solution was washed once with 6.7 L of 23% (w:w) aqueous sodium chloride
  11. dry with materialThe organinc solution was dried over 10 kg sodium sulfate
  12. filtrationfiltered
  13. customthe solvent removed on the rotary evaporator

Sources & evidence

ORD record
ord-1ce7691e3e604001aaddab9a0de2709b
Source dataset
uspto-grants-1998_06
Patent number
US05767144

Reaction notes

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