Hydrochloric Acid → HCID 54031970, compound

HRID 654338Notes

Reaction equation

HRID 654338 reaction equation
C(OC([O:6][C:7]1[CH:22]=[CH:21][C:10]([CH:11]=[CH:12][C:13]([O:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[O:14])=[CH:9][C:8]=1[O:23][CH3:24])=O)C.O.C(=O)([O-])[O-].[Na+].[Na+].Cl>CO>[OH:6][C:7]1[CH:22]=[CH:21][C:10]([CH:11]=[CH:12][C:13]([O:15][CH2:16][CH:17]=[C:18]([CH3:19])[CH3:20])=[O:14])=[CH:9][C:8]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 10340Sodium CarbonateHCID 54291562HCID 54291562, compound

Product 1

HCID 54031970HCID 54031970, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 60 ml of methanol is dissolved 1.78 g of prenyl 4-ethoxycarbonyloxy-3-methoxycinnamate. To the solution is added 15 ml of water followed by addition of 0.56 g of sodium carbonate. The mixture is stirred for 4 hours followed by addition of 100 ml of water and then 1N hydrochloric acid to acidify the mixture. The resulting mixture is extracted with chloroform, and the organic layer is washed with water and saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is distilled off under reduced pressure, and the residue is subjected to column chromatography on silica gel. From the fraction eluted with chloroform is obtained 1.02 g of prenyl 4-hydroxy-3-methoxycinnamate (5). Spectroscopic data of the product support the structure of the formula (5) below.

Workup

  1. extractionThe resulting mixture is extracted with chloroform
  2. washthe organic layer is washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent is distilled off under reduced pressure
  5. washFrom the fraction eluted with chloroform

Sources & evidence

ORD record
ord-ac599016dcde4bea8162bc1fc42f87bd
Source dataset
uspto-grants-1992_07
Patent number
US05130483

Reaction notes

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