Nitrogen → 1,6-Bis[4-(3-hydroxypropyl)phenoxy]hexane

HRID 1841295Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.I[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]I.N#N.[C:22](=[O:25])([O-])[O-].[K+].[K+]>CS(C)=O>[OH:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:22][OH:25])=[CH:4][CH:3]=2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3-(4-hydroxyphenyl)-1-propanol 35(3.3 g, 21.7 mmole) and 1,6-di-iodohexane (3.5 g 8.88 mmole) in dimethylsulfoxide (40 mL) was degassed and saturated with N2 gas and potassium carbonate 4.5 g, 32.56 mmole) was added. The reaction mixture was stirred at 80° C. for 18 h under nitrogen atmosphere and then quenched with brine (150 mL). The product was extracted with EtOAc (200 mL) and the organic extracts were washed with 0.1 M NaOH and brine, and dried with MgSO4. The organics were removed in vacuo to give a pale brown solid. The solid was purified by flash silica column chromatography: 4/1 hexane/EtOAc to 5% MeOH in 1/1 hexane/EtOAc to give 1,6-bis[4-(3-hydroxypropyl)phenoxy]hexane 36 (Rf=0.17 in 1/1 hexane/EtOAc) in 65% yield (2.23 g). 1H-NMR (CD3OD, 299.96 MHz): δ (ppm) 7.08-7.05 (d, 4H), 6.80-6.77 (d, 4H), 3.93-3.89 (t, 4H), 3.56-3.52 (t, 4H), 2.64-2.56 (t, 4H), 1.81-1.69 (m, 8H), 1.44-1.21 (m, 4H).

Workup

additionwas added
customquenched with brine (150 mL)
extractionThe product was extracted with EtOAc (200 mL)
washthe organic extracts were washed with 0.1 M NaOH and brine
dry with materialdried with MgSO4
customThe organics were removed in vacuo
customto give a pale brown solid
customThe solid was purified by flash silica column chromatography

Sources & evidence

ORD record: ord-b917523de9b24d03941ceebc3b9df230
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683115B2

Reaction notes

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