4-Coumaric acid → P-hydroxyl ethyl cinnaMate

HRID 1458296Notes

Reaction equation

HRID 1458296 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:23](O)[CH3:24]>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:23][CH3:24])=[O:9])=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 3224-Coumaric acidHCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 349172P-hydroxyl ethyl cinnaMate

Procedure

To a solution of 4- hydroxycinnamic acid (16.4 g) in ethanol (100 ml) was added sulfuric acid (10 ml). The mixture was refluxed with heating for 4 hours, Aqueous sodium bicarbonate solution was added to the reaction solution so as to make basic. Then, the reaction solution was extracted with chloroform. The extract was dried over sodium sulfate anhydride and then concentrated under a vacuum to yield a raw product of ethyl 4-hydroxycinnamate. In a manner similar to Reference Example 1, this raw product was reacted with geranyl bromide (21.7 g) and then hydrolyzed to yield 13.9 g (46%) of 4-geranyloxycinnamic acid.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 4 hours
  3. extractionThen, the reaction solution was extracted with chloroform
  4. dry with materialThe extract was dried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum

Sources & evidence

ORD record
ord-2d31f033a34d4c49b4c78350e5e55120
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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