Aluminum(III) Chloride → HCID 20442886, compound

HRID 1632449Notes

Reaction equation

HRID 1632449 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-8c2dc97bfd2c4c14bcda78959b4438a8
Source dataset
uspto-grants-1984_10
Patent number
US04475992

Reaction notes

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