p-Toluenesulfonic acid → HCID 54138557, compound

HRID 1728507Notes

Reaction equation

HRID 1728507 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH:24](O)[CH2:25][CH3:26])=[C:20]([F:28])[C:19]=3[F:29])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][CH3:26])=[C:20]([F:28])[C:19]=3[F:29])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19013830HCID 19013830, compound

Product 1

HCID 54138557HCID 54138557, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.2 g of 1-[4-(4-pentylphenyl)-phenyl]-2,3-difluoro-4(1-hydroxypropyl)-benzene and 0.3 g of p-toluenesulphonic acid in 70 ml of toluene is heated at reflux temperature for one hour, then cooled, washed with saturated sodium bicarbonate solution and dried over anhydrous magnesium sulphate. Evaporation of the solvent gives 1-[4-(4-pentylphenyl)phenyl]-2,3-difluoro-4-(1-propenyl)-benzene as a crude Z/E isomer mixture.

Workup

  1. temperatureat reflux temperature for one hour
  2. temperaturecooled
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e4574d4c00474e609e2ff8253fea54e3
Source dataset
uspto-grants-1994_07
Patent number
US05328637

Reaction notes

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