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

HRID 45475

Reaction equation

HRID 45475 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])(O)[CH3:26])[CH:20]=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]([CH3:17])([CH3:16])[CH3:18])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])=[CH2:26])[CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 582385991-(2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-yl)-1-(2-methoxyphenyl)ethanol

Product 1

HCID 582385762-(Benzyloxy)-3-tert-butyl-3'-(1-(2-methoxyphenyl)vinyl)biphenylYield 78%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of crude 37 (2.23 mmol) in toluene (80 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 (150 mL) and washed with saturated sodium bicarbonate (150 mL) and water (2×100 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 (75 g) with 2% ethyl acetate in heptane (4 L) to afford 38 (0.78 g, 78%).

Workup

  1. temperaturerefluxed under a Dean-Stark trap for 3 hr
  2. temperatureAfter cooling
  3. washwashed with saturated sodium bicarbonate (150 mL) and water (2×100 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 (75 g) with 2% ethyl acetate in heptane (4 L)

Sources & evidence

ORD record
ord-62a6c106885c494f8622bda6f18f757d
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Linked notes

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