Ethyl Acetate → HCID 118123634, compound

HRID 1500227Notes

Reaction equation

HRID 1500227 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](O)=[O:10])=[CH:5][CH:4]=1.S(Cl)([Cl:16])=O.[C:18]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:19]>>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([Cl:16])=[O:10])=[CH:5][CH:4]=1.[C:18]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 8857Ethyl Acetate2×HCID 132454-Methoxy cinnamic acid3×HCID 24386Thionyl Chloride

Product 1

HCID 118123634HCID 118123634, compoundYield 387.6%

Procedure

In a 100-mL three-neck flask, 3.1 g of 4-methoxycinnamic acid and 14.0 g of ethyl acetate were placed to give a suspension. The suspension was combined with 2.2 g of thionyl chloride (1.05 times the mole of 4-methoxycinnamic acid) added dropwise while maintaining the reactor inside temperature at 65° C. to 70° C. After the dropwise addition, a reaction was performed until the conversion from 4-methoxycinnamic acid reached 99% or more. After completion of reaction, 6.1 g of ethyl acetate was distilled off together with unreacted thionyl chloride and an acidic gas at 60° C. under reduced pressure. After the concentration, the resulting mixture was combined with ethyl acetate in an amount equal to the distilled-off amount and yielded 19.2 g of a 4-methoxycinnamoyl chloride/ethyl acetate solution (3).

Workup

  1. customto give a suspension
  2. additionadded dropwise
  3. temperaturewhile maintaining the reactor inside temperature at 65° C. to 70° C
  4. additionAfter the dropwise addition
  5. distillationwas distilled off together with unreacted thionyl chloride
  6. customat 60° C.
  7. concentrationAfter the concentration

Sources & evidence

ORD record
ord-fbae89cd4e56402da0327b7b86f158cc
Source dataset
uspto-grants-2015_12
Patent number
US09206138B2

Reaction notes

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