Potassium Iodide → 2-Methylbutyl 4'-(6-hydroxyhexyloxy)biphenyl-4-carboxylate

HRID 1085758Notes

Reaction equation

HRID 1085758 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH:18]([CH3:21])[CH2:19][CH3:20])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35].[I-].[K+]>CC(C)=O>[OH:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH:18]([CH3:21])[CH2:19][CH3:20])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanolHCID 139075372-Methylbutyl 4'-hydroxybiphenyl-4-carboxylate

Product 1

HCID 200588202-Methylbutyl 4'-(6-hydroxyhexyloxy)biphenyl-4-carboxylateYield 34.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.84 g of 2-methylbutyl 4'-hydroxybiphenyl-4-carboxylate, 4.14 g of potassium carbonate, 4.10 g of 6-chloro-1-hexanol and 4.28 g of potassium iodide were heat-refluxed for 48 hours in acetone. The mixture was subjected to filtration, condensation and purification by column chromatography to obtain 1.31 g of the objective product (yield: 34%).

Workup

  1. filtrationThe mixture was subjected to filtration, condensation and purification by column chromatography

Sources & evidence

ORD record
ord-1a1e807bed6f49adba1260129a0ac7ed
Source dataset
uspto-grants-1991_04
Patent number
US05011623

Reaction notes

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