p-Toluenesulfonic acid → 3'-(1-(2-(Benzyloxy)biphenyl-3-yl)vinyl)-2-methoxybiphenyl

HRID 45457Notes

Reaction equation

HRID 45457 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[CH:21]=[CH:22][CH:23]=2)(O)[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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]([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[CH:21]=[CH:22][CH:23]=2)=[CH2:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 582385901-(2-(Benzyloxy)biphenyl-3-yl)-1-(2'-methoxybiphenyl-3-yl)ethanol

Product 1

HCID 582386073'-(1-(2-(Benzyloxy)biphenyl-3-yl)vinyl)-2-methoxybiphenylYield 40.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of crude 22 (2.66 mmol) in toluene (60 mL) was treated with para-toluenesulfonic acid (20 mg) and refluxed under a Dean-Stark trap for 1.5 hrs. After cooling, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated sodium bicarbonate (100 mL) and water (100 mL). The solvent was removed in a rotary evaporator and the crude product was purified by chromatography on silica (40 g) with hexane (2 L) and 1% ethyl acetate in hexane (2 L) to afford pure 23 (0.12 g) and impure 23 (0.50 g).

Workup

  1. temperaturerefluxed under a Dean-Stark trap for 1.5 hrs
  2. temperatureAfter cooling
  3. washwashed with saturated sodium bicarbonate (100 mL) and water (100 mL)
  4. customThe solvent was removed in a rotary evaporator
  5. customthe crude product was purified by chromatography on silica (40 g) with hexane (2 L) and 1% ethyl acetate in hexane (2 L)

Sources & evidence

ORD record
ord-b050087d9118449780dfc724b2cd31c0
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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