Perchloric Acid → HCID 20442879, compound

HRID 2296526Notes

Reaction equation

HRID 2296526 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:12][CH3:13])([O:9][CH2:10][CH3:11])[C:7]([O:14][CH3:15])=[CH:6][C:5](OCC)([CH3:16])[CH:4]=1.Cl(O)(=O)(=O)=O>C(Cl)Cl>[CH3:15][O:14][C:7]1[C:8]([O:12][CH3:13])([O:9][CH2:10][CH3:11])[C:3]([O:2][CH3:1])=[CH:4][C:5](=[CH2:16])[CH:6]=1

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 20442877HCID 20442877, compound

Product 1

HCID 20442879HCID 20442879, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same procedure as in Example 9 was repeated using 272 mg of 1,5,6-trimethoxy-3,6-diethoxy-3-methyl-1,4-cyclohexadiene, 10 mg of methylene chloride and 10 mg of perchloric acid recovering 230 mg of an oily crude product. The crude product was purified by silica gel column chromatograph using a 20:1 benzene-ethyl acetate mixture giving 220 mg of 1,5,6-trimethoxy-6-ethoxy-3-methylidene-1,4-cyclohexadiene in 92% of theoretical yield. The compound thus obtained was identified by NMR.

Workup

  1. customThe crude product was purified by silica gel column chromatograph

Sources & evidence

ORD record
ord-492dce58b4754d9094d91e75d5d74360
Source dataset
uspto-grants-1984_01
Patent number
US04429164

Reaction notes

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