Methanol → 5-(2-(4-Hydroxyphenyl)Ethenyl)Benzene-1,3-Diol

HRID 1163277Notes

Reaction equation

HRID 1163277 reaction equation
C(O[C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]2[CH:18]=CC=[CH:15][CH:14]=2)=[C:7](OC(=O)C)[C:6]=1[O:23]C(=O)C)(=O)C.[C:27]([O-:30])(=O)[CH3:28].[NH4+].C[OH:33]>>[C:8]1([CH:11]=[CH:12][C:13]2[CH:18]=[CH:28][C:27]([OH:30])=[CH:15][CH:14]=2)[CH:7]=[C:6]([OH:23])[CH:5]=[C:10]([OH:33])[CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 517165Ammonium AcetateHCID 67170930HCID 67170930, compound

Product 1

HCID 50565-(2-(4-Hydroxyphenyl)Ethenyl)Benzene-1,3-DiolYield 97%

Conditions

Temperature
5 °C

Procedure

2.10 g (6.0 mmol) triacetoxystilbene were dissolved under reflux in 19.3 ml methanol and 39 ml ammonium acetate solution (25%) was added to the solution. The reaction mixture was stirred for three hours at the same temperature and afterwards the methanol was distilled off. By cooling to 5° C. the product crystallized and could be filtered off. 1.33 g (5.82 mmol, 97%) resveratrol were obtained as a pure compound. The mother liquor was purified by extraction with methyl-butyl-ether and neutralized with ammonia. After concentration under reduced pressure the solution was used again for the described reaction.

Workup

  1. distillationafterwards the methanol was distilled off
  2. customcrystallized
  3. filtrationcould be filtered off

Sources & evidence

ORD record
ord-a39cd5814b8e4cfb83a268c64010e173
Source dataset
uspto-grants-2010_10
Patent number
US07820848B2

Reaction notes

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