HCID 22401893, compound → HCID 14986483, compound

HRID 654718Notes

Reaction equation

HRID 654718 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:15][CH2:16][CH3:17])[C:8](/[CH:18]=[C:19](\[CH3:23])/[C:20]([OH:22])=[O:21])=[CH:7][C:6]=1[O:24][CH3:25])(=[O:3])[CH3:2]>CC(C)=O>[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:15][CH2:16][CH3:17])[C:8](/[CH:18]=[C:19](/[CH3:23])\[C:20]([OH:22])=[O:21])=[CH:7][C:6]=1[O:24][CH3:25])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 22401893HCID 22401893, compound

Product 1

HCID 14986483HCID 14986483, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7.4 g of (E)-3-(4-acetoxy-3-methoxy-5-propyl-1-naphthyl)-2-methylpropenoic acid was dissolved in 1.3 liters of acetone, and irradiated with light from a high pressure mercury lamp through a Pyrex filter at room temperature for 3 hours. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography (3% methanol/chloroform) to obtain 2.7 g of the titled compound as colorless crystals.

Workup

  1. customirradiated with light from a high pressure mercury lamp through a Pyrex
  2. filtrationfilter at room temperature for 3 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by silica gel column chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-a12a11b20f1b41e58b9956468684156f
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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