Chlorotrimethylsilane → 2-(4-Methoxybenzyl)phenol

HRID 1182027Notes

Reaction equation

HRID 1182027 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=O.C[Si](Cl)(C)C.C([BH3-])#N.[Na+]>C(#N)C.ClCCl>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[OH:1])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 87768Benzophenone, 2-hydroxy-4'-methoxy-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 2584512-(4-Methoxybenzyl)phenol

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.78 g of (2-hydroxyphenyl)(4-methoxyphenyl)methanone is dissolved in acetonitrile and cooled to 0° C. 2 ml of TMSCl are added dropwise to the mixture, and then 1 g of sodium cyanoborohydride is added. The mixture is stirred at room temperature for 3 h. The reaction solution is diluted with dichloromethane and filtered through Celite.

Workup

  1. filtrationfiltered through Celite

Sources & evidence

ORD record
ord-6b62814bfb4949bd98a1936ad814fe05
Source dataset
uspto-grants-2007_10
Patent number
US07288528B2

Reaction notes

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