Sodium Hydroxide → (+/-)-(E)-1-(4-(2-Phenylethenyl)phenoxy)-4-(3-pyridyl)-2-butanol

HRID 1600949Notes

Reaction equation

HRID 1600949 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Cl[CH2:17][CH:18]([OH:27])[CH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.[OH-].[Na+]>C(O)C.O>[C:10]1(/[CH:9]=[CH:8]/[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:17][CH:18]([OH:27])[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:7][CH:6]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5284650trans-4-HydroxystilbeneHCID 22465338HCID 22465338, compound

Product 1

HCID 21830666(+/-)-(E)-1-(4-(2-Phenylethenyl)phenoxy)-4-(3-pyridyl)-2-butanolYield 40.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Prepared according to the method described in Example 24b) from trans-4-hydroxystilbene (2.6 g), (±)-α-(chloromethyl)-3-pyridinepropanol (2.5 g) and sodium hydroxide (0.54 g) in ethanol (50 ml) and water (10 ml) at reflux for 2 hours to give the title compound as a solid (1.84 g)

Workup

  1. customPrepared
  2. temperatureat reflux for 2 hours

Sources & evidence

ORD record
ord-c48cd6cd2b2445d48769a1545ad2b039
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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