p-Toluenesulfonic acid → HCID 18434141, compound

HRID 2306471Notes

Reaction equation

HRID 2306471 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)(O)[CH3:9])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[CH2:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18434188HCID 18434188, compound

Product 1

HCID 18434141HCID 18434141, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ef) 6.6 g of (RS)-4-[1-(4-bromo-phenyl)-1-hydroxy-ethyl]-phenol (Ex. Ea) are dissolved in 50 ml of ethanol, boiled under reflux with 0.34 g of p-toluenesulphonic acid and then evaporated at 30° C. The residue is treated with 150 ml of saturated sodium carbonate solution and extracted with ethyl acetate. The organic phases are washed with saturated sodium chloride solution, dried and evaporated. Purification on silica gel with ethyl acetate-hexane (20:80) as the eluent gives 4.1 g of 4-[1-(4-bromo-phenyl)-vinyl]-phenol MS: m/e 274 (M+H+, 1Br).

Workup

  1. customevaporated at 30° C
  2. additionThe residue is treated with 150 ml of saturated sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe organic phases are washed with saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customPurification on silica gel with ethyl acetate-hexane (20:80) as the eluent

Sources & evidence

ORD record
ord-fa7d5d7a70954a09b58d3ba2a37f4b21
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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