2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Asarone

HRID 1357366Notes

Reaction equation

HRID 1357366 reaction equation
[CH3:1]/[CH:2]=[CH:3]/[C:4]1[CH:15]=[C:12]([O:13][CH3:14])[C:9]([O:10][CH3:11])=[CH:8][C:5]=1[O:6][CH3:7].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[CH:20][C:19]=1[CH2:28][CH2:29][CH3:30].C(C1C(=O)C(Cl)=C(Cl)C(=[O:36])C=1C#N)#N>>[CH3:1]/[CH:2]=[CH:3]/[C:4]1[CH:15]=[C:12]([O:13][CH3:14])[C:9]([O:10][CH3:11])=[CH:8][C:5]=1[O:6][CH3:7].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[CH:20][C:19]=1/[CH:28]=[CH:29]/[CH:30]=[O:36]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 636822Asarone2×HCID 9877746Benzene, 1,2,4-trimethoxy-5-propyl-

Product 2

HCID 636822AsaroneHCID 98132662,4,5-Trimethoxycinnamaldehyde

Procedure

Preparation of α-asarone via dehydrogenation of 2,4,5-trimethoxyphenylpropane with DDQ containing little amount of silica gel: Addition of a catalytic amount of silica gel (0.2-0.6 g) drastically accelerated the rate of reaction as well as improved the yield of α-asarone when above dehydrogenation process (Example II-a) was conducted under the same condition resulting α-asarone in 72% yield and trans-2,4,5-trimethoxycinnamaldehyde in 18% yield.

Workup

  1. additionAddition of a catalytic amount of silica gel (0.2-0.6 g)
  2. customthe rate of reaction as well

Sources & evidence

ORD record
ord-97e8dd97db734c84b0366cf2bfa470d4
Source dataset
uspto-grants-2003_07
Patent number
US06590127B1

Reaction notes

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