4-Hydroxybenzyl Alcohol → 4-(4-Allyldimethylsilylbenzyloxy)benzyl Alcohol

HRID 2228384Notes

Reaction equation

HRID 2228384 reaction equation
[CH2:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8](Br)[SiH:9]([CH3:11])[CH3:10])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH2:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]([SiH:9]([CH3:11])[CH3:10])[O:15][C:16]2[CH:23]=[CH:22][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=2)=[CH:6][CH:5]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 11430Potassium CarbonateHCID 1317233674-Allyldimethylsilylbenzyl bromide

Product 1

HCID 1317233814-(4-Allyldimethylsilylbenzyloxy)benzyl AlcoholYield 94%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

A solution of 4-allyldimethylsilylbenzyl bromide (4 Scheme 13, 2.7 g, 10 mmol), 4-hydroxybenzyl alcohol (12.5 g, 10 mmol), tetrabutylammonium iodide (100 mg) and powdered K2CO3 (2.1 g, 15 mmol) in acetone (60 mL) was stirred at 60° C. for 22 h. The precipitated sol was filtered and the filtrate was concentrated. The crude oil was purified by column chromatography (1:3 ethyl acetate/hexanes) to afford a colorless oil (2.9 g, 94%); 1H NMR (300 MHz, CDCl3) δ 0.37 (s, 6 H), 1.84 (d, J=6.30 Hz, 2 H), 2.72 (s, OH, 1 H), 4.58 (s, 2 H), 4.93 (s, 1 H), 4.97 (m, 2 H), 5.09 (s, 1 H), 5.86 (ddt, J=16.80 Hz, 10.50, 8.10 Hz, 1 H), 7.01 (d, J=8.40 Hz, 2 H), 7.30 (d, J=8.40 Hz, 2 H), 7.48 (d, J=7.90 Hz, 2 H), 7.61 (d, J=7.90 Hz, 2 H); 13C NMR (75 MHz, CDCl3) −3.1 (2 C), 24.0, 65.0, 70.2, 113.9, 115.2 (2 C), 127.1 (2 C), 128.9 (2 C), 133.8, 134.2 (2 C), 134.8, 138.1, 138.7, 158.6. HRMS (EI) calcd for C19H24O2Si 312.1545, found 312.1547.

Workup

  1. filtrationThe precipitated sol was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude oil was purified by column chromatography (1:3 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fe9a38d07c1e4c5d9ee03514eaf2f1ec
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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