Sulfuric Acid → 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester

HRID 1840655Notes

Reaction equation

HRID 1840655 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=O)=[CH:7][CH:8]=1.[C:11]([O:14][CH3:15])(=[O:13])[CH3:12].C[O-].[Na+].S(=O)(=O)(O)O>CCCCCCC.C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:4]([CH:3]([CH2:8][CH2:7][CH2:6][CH3:9])[CH2:15][O:14][C:11](=[O:13])[CH:12]=[CH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:5]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 6584Methyl AcetateHCID 312444-MethoxybenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 216302-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl esterYield 83%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

U.S. Pat. No. 5,527,947 describes a process in which C1-C4-alkoxybenzaldehydes, such as anisaldehyde, and C1-C4-alkyl acetates, such as methyl acetate, are dissolved in an inert hydrocarbon, such as heptane, toluene or petroleum ether. In the presence of a strongly alkaline metal base, such as sodium methoxide, the feed substances react to give a mixture of the corresponding C1-C4-alkyl-C1-C4-alkoxy cinnamates, the alkali metal salts of the corresponding C1-C4-alkoxy cinnamic acid and the C1-C4-alkanols. Following acidification of the reaction mixture with a strong polybasic acid, such as sulfuric acid, the liberated acetic acid is esterified with the C1-C4-alkanoles and distilled off. The mixture of C1-C4-alkyl-C1-C4-alkoxycinnamates and C1-C4-alkoxycinnamic acids which remains is reacted with a C5-C14-alkanol in the presence of a metal salt of a strong polybasic acid, such as sulfuric acid. Following transesterification and esterification, the corresponding C5-C14-alkyl-C1-C4-alkoxycinnamate, e.g. 2-ethylhexyl-4-methoxycinnamate, is obtained with 83 to 87% yield.

Workup

  1. customto give
  2. distillationdistilled off
  3. additionThe mixture of C1-C4-alkyl-C1-C4-alkoxycinnamates and C1-C4-alkoxycinnamic acids which
  4. customremains is reacted with a C5-C14-alkanol in the presence of a metal salt of a strong polybasic acid, such as sulfuric acid

Sources & evidence

ORD record
ord-f2e86aab657d4d50b7d5e75e13b677b2
Source dataset
uspto-grants-2004_01
Patent number
US06680404B1

Reaction notes

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