Nitrogen → Racemic 1,3,5-Tris(1-(4-hydroxyphenyl)ethyl)benzene

HRID 41719Notes

Reaction equation

HRID 41719 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[C:15]([CH:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)[CH3:18])[CH:14]=[C:13]([CH:27]([C:29]3[CH:34]=[CH:33][C:32]([O:35]C)=[CH:31][CH:30]=3)[CH3:28])[CH:12]=2)[CH3:10])=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1.N#N>O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[C:15]([CH:17]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[CH3:18])[CH:14]=[C:13]([CH:27]([C:29]3[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=3)[CH3:28])[CH:12]=2)[CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 10176127Pyridinium chlorideHCID 89785327Racemic 1,3,5-Tris(1-(4-methoxyphenyl)ethyl)benzene

Product 1

HCID 89785314Racemic 1,3,5-Tris(1-(4-hydroxyphenyl)ethyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A 250 mL round-bottomed flask equipped with magnetic stirring bar was charged with racemic 1,3,5-tris(1-(4-methoxyphenyl)ethyl)benzene (5) (19.6 g, 41 mmol) and pyridine hydrochloride (56.8 g, 0.49 mol, 12 equiv). The mixture was protected with an N2 bubbler and heated in a 180° C. oil bath for 5 h. The mixture was allowed to cool briefly to ˜120° C. and then 55° C. H2O (100 mL) was added slowly to the mixture with vigorous stirring. The mixture was extracted three times with EtOAc (100 mL portions). The collected organic phase was washed with brine (200 mL) and dried over anhydrous MgSO4. Rotary evaporation gave a thick, colorless oil that foamed under vacuum. Yield: 17.17 g (95%). 1H NMR (300 MHz, DMSO-d6, δ, ppm): 9.12 (s, 3OH), 6.98 (d, J=8.6 Hz, 6H), 6.90 (s, 3H), 6.63 (d, J=8.6 Hz, 6H), 3.92 (q, J=7.2 Hz, 3H), 1.44 (d, J=7.5 Hz, 9H). 13C NMR (75 MHz, DMSO-d6, δ, ppm): 155.35, 146.59, 146.53, 146.48, 136.69, 136.67, 136.65, 128.04, 123.88, 123.65, 114.96, 43.49, 43.46, 22.09, 22.04. Anal. calcd for C30H30O3.0.65H2O: C, 80.02; H, 7.01. Found: C, 80.38; H, 7.41.

Workup

  1. customA 250 mL round-bottomed flask equipped with magnetic stirring bar
  2. temperatureto cool briefly to ˜120° C.
  3. custom55° C
  4. extractionThe mixture was extracted three times with EtOAc (100 mL portions)
  5. washThe collected organic phase was washed with brine (200 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. customRotary evaporation
  8. customgave a thick, colorless oil

Sources & evidence

ORD record
ord-c9e3914060f24c62a6cb1c41adc4ccbc
Source dataset
uspto-grants-2013_09
Patent number
US08530693B1

Reaction notes

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