HCID 10361925, compound → HCID 9972006, compound

HRID 488138Notes

Reaction equation

HRID 488138 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:20]=[C:21](\[CH3:27])/[C:22]([O:24]CC)=[O:23])[C:6]2[C:11]([C:12]=1[O:13]COC)=[C:10]([CH2:17][CH2:18][CH3:19])[CH:9]=[CH:8][CH:7]=2>CC(C)=O>[OH:13][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:17][CH2:18][CH3:19])[C:5](/[CH:20]=[C:21](/[CH3:27])\[C:22]([OH:24])=[O:23])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

3

Reactant 1

HCID 10361925HCID 10361925, compound

Product 1

HCID 9972006HCID 9972006, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

196.5 g of ethyl (E)-3-(3-methoxy-4-methoxymethoxy-5-propyl-1-naphthyl)-2-methylpropenoate was dissolved in 2.6 liters of acetone and irradiated with light from a high pressure mercury lamp through a Pyrex filter for 2.5 hours. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography (3% ethyl acetate/hexane) to obtain 59.2 g of the titled compound as a pale yellow oil. At the same time, 136.4 g of a mixture of the E and Z isomers was recovered.

Workup

  1. customirradiated with light from a high pressure mercury lamp through a Pyrex
  2. filtrationfilter for 2.5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by silica gel column chromatography (3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f829e01e8adc49848de086dbe66b3e7e
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

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