2-Ethylhexyl glycidyl ether → 1-[4-(1,1-Dioxo-thiomorpholin-4-yl)-phenoxy]-3-(2-ethylhexyloxy)-propan-2ol

HRID 619093

Reaction equation

HRID 619093 reaction equation
[O:1]=[S:2]1(=[O:15])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH2:16]([O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])[CH:17]1[O:19][CH2:18]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[O:15]=[S:2]1(=[O:1])[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:18][CH:17]([OH:19])[CH2:16][O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 171622-Ethylhexyl glycidyl etherHCID 218452234-(4-Hydroxyphenyl)thiomorpholine 1,1-Dioxide

Product 1

HCID 190806361-[4-(1,1-Dioxo-thiomorpholin-4-yl)-phenoxy]-3-(2-ethylhexyloxy)-propan-2olYield 70%

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

4-(1,1-dioxo-thiomorpholin-4-yl)phenol (4.1 g, 18 mmol), 2-ethylhexyl glycidyl ether (4.4 g, 23,6 mmol) and ethyltriphenylphosphonium bromide (0.37 g) are heated under nitrogen for 5 h at 145° C. and the crude product is chromatographed over silica gel (hexane/ethylacetate 1:1) to afford a colourless liquid 5.2 g (70%).

Workup

  1. customthe crude product is chromatographed over silica gel (hexane/ethylacetate 1:1)

Sources & evidence

ORD record
ord-39b458af6e5e42c3b9cba30a11e20b0c
Source dataset
uspto-grants-1999_09
Patent number
US05958663

Linked notes

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