Bis(4-hydroxyphenyl)methane → (+/-)-alpha-(4-(4-Hydroxyphenylmethyl)phenoxymethyl)-3-pyridinepropanol

HRID 1600896Notes

Reaction equation

HRID 1600896 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[O:16]1[CH2:18][CH:17]1[CH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.[H-].[Na+]>CN(C)C=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:18][CH:17]([OH:16])[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 12111Bis(4-hydroxyphenyl)methaneHCID 24758Sodium hydrideHCID 10877288HCID 10877288, compound

Product 1

HCID 21830676(+/-)-alpha-(4-(4-Hydroxyphenylmethyl)phenoxymethyl)-3-pyridinepropanolYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method described in Example 5 from bis(4-hydroxyphenyl)methane (1.6 g), (±)-3-(2-oxiranylethyl)pyridine (1.24 g) and sodium hydride (60% dispersion in oil; 0.319 g) in dimethylformamide (25 ml) at 100° C. for 2 hours to give the title compound as a white solid (0.587 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8350cbd0cb044069ac11de123dfbf446
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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