Isoeugenol → 4-hydroxy-3-methoxyphenyl-7-methoxy3-methyl-5-(E)-propenylbenzofuran

HRID 1659554Notes

Reaction equation

HRID 1659554 reaction equation
[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)/[CH:7]=[CH:8]/[CH3:9])[OH:3]>O.C(O)C>[OH:3][C:2]1[CH:4]=[CH:5][C:6]([C:7]2[O:3][C:2]3[C:1]([O:11][CH3:12])=[CH:10][C:6](/[CH:7]=[CH:8]/[CH3:9])=[CH:5][C:4]=3[C:8]=2[CH3:9])=[CH:10][C:1]=1[O:11][CH3:12]

Participants

4

Reactant 1

HCID 853433Isoeugenol

Product 1

HCID 103141754-hydroxy-3-methoxyphenyl-7-methoxy3-methyl-5-(E)-propenylbenzofuran

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

150 g ferric chloride in 400 ml water are added to a solution of 100 g (E)-isoeugenol in 1.3 liter 75 percent ethanol and allowed to stand for 24 hours at 0° C. The resulting sediment is filtered off and recrystallized from ethanol, resulting in 53 g trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl-7-methoxy3-methyl-5-(E)-propenylbenzofuran ("dehydrodiisoeugenol") as colorless crystals; melting point 132°-133° C.

Workup

  1. filtrationThe resulting sediment is filtered off
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1d89cf11714141fd9a7e0bf7dcf364b8
Source dataset
uspto-grants-1981_12
Patent number
US04304785

Reaction notes

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