Aluminum(III) Chloride → HCID 20442886, compound

HRID 2296527Notes

Reaction equation

HRID 2296527 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])([O:12][CH3:13])[C:10]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:9][C:8](OC)([CH3:24])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[Cl-].[Al+3].[Cl-].[Cl-]>CCOCC>[CH2:20]([O:19][C:10]1[C:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])([O:12][CH3:13])[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][C:8](=[CH2:24])[CH:9]=1)[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 20442870HCID 20442870, compound

Product 1

HCID 20442886HCID 20442886, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The procedure of Example 9 was repeated by using 334 mg of 1,5,6-tributoxy-3,6-dimethoxy-3-methyl-1,4-cyclohexadiene, 10 ml of ether and 15 mg of aluminum chloride, recovering 290 mg of an oily crude product. The crude product was purified by silica gel column chromatography using a 20:1 benzene-ethyl acetate mixture, giving 268 mg of 1,5,6-tributoxy-6-methoxy-3-methylidene-1,4-cyclohexadiene in 89% of the theoretical yield. The compound thus obtained was identified by NMR.

Workup

  1. customrecovering 290 mg of an oily crude product
  2. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0e31b9f896384b1aa1d365ec7ae63fd3
Source dataset
uspto-grants-1984_01
Patent number
US04429164

Reaction notes

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