Tyrosol → HCID 54139691, compound

HRID 862855Notes

Reaction equation

HRID 862855 reaction equation
[O-]CC.[Na+].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][OH:14])=[CH:8][CH:7]=1.[CH2:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22]>C(O)C.O1CCCC1>[CH2:22]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][OH:14])=[CH:8][CH:7]=1)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 10393TyrosolHCID 759078-Bromooct-1-eneHCID 2723922Sodium ethoxide

Product 1

HCID 54139691HCID 54139691, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Sodium ethoxide (4.98 g) was added to a solution (240 ml) of 2-(4-hydroxyphenyl)ethyl alcohol (8.68 g) in absolute ethanol and the mixture was stirred at 50° C. for 30 minutes. A solution of 7-octenyl bromide (10 g) in anhydrous tetrahydrofuran was dropwise added thereto and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was concentrated, poured into ice water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel chromatography (eluent; ethyl acetate:hexane=1:5) to give the subject compound (10.76 g) as an oily substance.

Workup

  1. stirringthe mixture was stirred at 50° C. for 6 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionpoured into ice water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled away
  8. customthe residue was purified by silica gel chromatography (eluent; ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-b90c38d0b4ac427283c7783f2fac2059
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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