Hydrochloric Acid → HCID 54364024, compound

HRID 654339Notes

Reaction equation

HRID 654339 reaction equation
C(OC([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][CH:15]=[CH:16][C:17]([O:19][CH2:20][CH:21]=[C:22]([CH2:24][CH2:25][CH:26]=[C:27]([CH2:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])[CH3:28])[CH3:23])=[O:18])=[CH:9][C:8]=1[O:35][CH3:36])=O)C.O.C(=O)([O-])[O-].[Na+].[Na+].Cl>CO>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][CH:15]=[CH:16][C:17]([O:19][CH2:20][CH:21]=[C:22]([CH2:24][CH2:25][CH:26]=[C:27]([CH2:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])[CH3:28])[CH3:23])=[O:18])=[CH:9][C:8]=1[O:35][CH3:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 10340Sodium CarbonateHCID 54368424HCID 54368424, compound

Product 1

HCID 54364024HCID 54364024, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.38 g of farnesyl 5-(4-ethoxycarbonyloxy-3-methoxyphenyl)-2,4-pentadienoate in 10 ml of methanol are added 2 ml of water and 0.08 g of sodium carbonate followed by stirring for 3 hours. To the reaction mixture is added 10 ml of water. The mixture is acidified with 1N hydrochloric acid and then extracted with chloroform. The organic layer is washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure, and the residue is subjected to column chromatography on silica gel. From the fraction eluted with chloroform is obtained 0.22 g of farnesyl 5-(4-hydroxy-3-methoxyphenyl)-2,4-pentadienoate (10). Spectroscopic data of the product support the structure of the formula (10) below.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer is washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent is then distilled off under reduced pressure
  5. washFrom the fraction eluted with chloroform

Sources & evidence

ORD record
ord-222e61ef68d04bceadd17fd1f440d3d7
Source dataset
uspto-grants-1992_07
Patent number
US05130483

Reaction notes

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