Thiophenol → 3-Thiophenoxymethyl-5-t-octylcatechol

HRID 2107755

Reaction equation

O1CCN([CH2:7][C:8]2[CH:14]=[C:13]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:16])[CH:12]=[C:10]([OH:11])[C:9]=2[OH:23])CC1.[C:24]1([SH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O.C(OCC)C>[S:30]([CH2:7][C:8]1[CH:14]=[C:13]([C:15]([CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:16])[CH3:17])[CH:12]=[C:10]([OH:11])[C:9]=1[OH:23])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of 3-morpholinomethyl-5-t-octylcatechol (564 g, 1.76 mole) and 193.4 g (1.76 mole) benzenethiol in 0.8 liter dimethylformamide was kept at 130° C. under a nitrogen atmosphere for 20 hours. The reaction mixture was cooled to 25° C. and diluted with 3000 ml diethyl ether. The resulting solution was washed in turn with 3×1000 ml water, 500 ml 10% hydrochloric acid, 500 ml water and 500 ml brine. The washed solution was dried over anhydrous magnesium sulfate and evaporated in vacuo to a yellow oil (548.9 g, 91% yield) of the title compound.

Workup

washThe resulting solution was washed in turn with 3×1000 ml water, 500 ml 10% hydrochloric acid, 500 ml water and 500 ml brine
dry with materialThe washed solution was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record: ord-9a475c94d5ff439b8cd788d1a8d30391
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04935442

Linked notes

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