Acetic Acid → HCID 53811930, compound

HRID 344931Notes

Reaction equation

HRID 344931 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]2[CH:16]=[C:15]([CH2:17][CH:18]=[CH2:19])[CH:14]=[CH:13][C:12]=2[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br)[CH:5]=1)[CH:2]=[CH2:3].[C:28]([OH:31])(=[O:30])[CH3:29]>C([O-])(=O)C.[Ag+]>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]2[CH:16]=[C:15]([CH2:17][CH:18]=[CH2:19])[CH:14]=[CH:13][C:12]=2[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:31][C:28](=[O:30])[CH3:29])[CH:5]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 53646384HCID 53646384, compound

Product 1

HCID 53811930HCID 53811930, compound

Reagents, catalysts & solvents 1

HCID 11246Silver acetateCatalyst

Procedure

A mixture was prepared by adding 0.2 g of 4-allyl-2-[5-allyl- 2-(6-bromohexyloxy)phenyl]phenol and 0.1 g of silver acetate to 3 ml of acetic acid. The mixture was refluxed by heating for 2 hours and concentrated. The concentrate was extracted with diethylether. The extract was washed with solution sodium hydrogencarbonate and an aqueous solution saturated with NaCl, dried with sodium sulfate and concentrated. The concentrate was purified by a silica gel column-chromatography (n-hexane:ethyl acetate=15:1) to yield 0.12 g of 4-allyl-2-[5allyl-2-(6-acetoxyhexyloxy)phenyl]phenol.

Workup

  1. customA mixture was prepared
  2. temperatureThe mixture was refluxed
  3. temperatureby heating for 2 hours
  4. concentrationconcentrated
  5. extractionThe concentrate was extracted with diethylether
  6. washThe extract was washed with solution sodium hydrogencarbonate
  7. dry with materialan aqueous solution saturated with NaCl, dried with sodium sulfate
  8. concentrationconcentrated
  9. customThe concentrate was purified by a silica gel column-chromatography (n-hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-2bc4295ada254a2f86e82359ce989a01
Source dataset
uspto-grants-1991_10
Patent number
US05053548

Reaction notes

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