Sodium Iodide → 3-Cyclopentyloxy-4-methoxybenzyl alcohol

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][OH:6].[CH:12]1(OBr)[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>>[CH:12]1([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][CH3:11])[CH2:5][OH:6])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Reactant 4

HCID 5238Sodium Iodide

HCID 10796Cesium carbonate

HCID 780893-Hydroxy-4-methoxybenzyl alcohol

HCID 21697665Cyclopentyloxy-bromide

Product 1

HCID 111387063-Cyclopentyloxy-4-methoxybenzyl alcoholYield 35.8%

Procedure

From 3-hydroxy-4-methoxybenzyl alcohol (50 g, 0.324 mol), cyclopentyloxybromide (70 ml, 0.648 mol), caesium carbonate (72.83 g, 0.222 mol) and sodium iodide (5.63 g, 0.037 mol). Chromatography (SiO2; EtOAc—C6H14. 1:3) to yield the title compound (25.782 g). (Found C, 69.92; H, 8.18. C13H18O3 requires C, 70.25; H, 8.16).