(E)-3-(4-acetoxy-5-ethyl-3-methoxy-1-naphthyl)-2-methylpropenoic acid → E 5090

HRID 488134Notes

Reaction equation

HRID 488134 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][CH3:16])[C:8](/[CH:17]=[C:18](\[CH3:22])/[C:19]([OH:21])=[O:20])=[CH:7][C:6]=1[O:23][CH3:24])(=[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][CH3:16])[C:8](/[CH:17]=[C:18](/[CH3:22])\[C:19]([OH:21])=[O:20])=[CH:7][C:6]=1[O:23][CH3:24])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 6505040(E)-3-(4-acetoxy-5-ethyl-3-methoxy-1-naphthyl)-2-methylpropenoic acid

Product 1

HCID 6438616E 5090Yield 40.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.15 g of (E)-3-(4-acetoxy-5-ethyl-3-methoxy-1-naphthyl)-2-methylpropenoic acid was dissolved in 200 ml 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 470 mg 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-4e68f7a3e46c4e7e9c03fad0d13a0691
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

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