p-Toluenesulfonic acid → 2-(Benzyloxy)-3-phenyl-3'-(1-(2-methoxyphenyl)vinyl)biphenyl

HRID 45471Notes

Reaction equation

HRID 45471 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH3:37])(O)[CH3:28])[CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH3:37])=[CH2:28])[CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 582386031-(2'-(Benzyloxy)-3'-phenybiphenyl-3-yl)-1-(2-methoxyphenyl)ethanol

Product 1

HCID 582385932-(Benzyloxy)-3-phenyl-3'-(1-(2-methoxyphenyl)vinyl)biphenylYield 62%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of crude 33 (3.96 mol) in toluene (150 mL) was treated with p-toluenesulfonic acid (100 mg) and refluxed under a Dean-Stark trap for 3 hr. After cooling, the reaction mixture was diluted with ethyl acetate (80 mL) and washed with saturated sodium bicarbonate (80 mL) and water (2×80 mL). The organic extract was dried over sodium sulfate and filtered. The solvent was removed in a rotary evaporator and the crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (2 L) to afford 34 (1.15 g, 62%).

Workup

  1. temperaturerefluxed under a Dean-Stark trap for 3 hr
  2. temperatureAfter cooling
  3. washwashed with saturated sodium bicarbonate (80 mL) and water (2×80 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in a rotary evaporator
  8. customthe crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (2 L)

Sources & evidence

ORD record
ord-21824df276cc418fb8868cfd8d70b4c2
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

Loading…