1-Hexanol → HCID 22506159, compound

HRID 1814403Notes

Reaction equation

FC(F)(F)S(O)(=O)=O.[CH2:9]1[CH2:19][CH2:18]N2[C:12](=NCCC2)[CH2:11][CH2:10]1.[CH2:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[CH3:27][Si:28]([CH3:35])([OH:34])[O:29][Si:30]([CH3:33])([CH3:32])O>C1(C)C=CC=CC=1>[CH2:20]([O:26][Si:30]([CH3:33])([CH3:32])[O:29][Si:28]([O:34][CH2:18][CH2:19][CH2:9][CH2:10][CH2:11][CH3:12])([CH3:35])[CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 35 °C

Procedure

A 100-ml four-necked flask equipped with a Dimroth condenser, stirrer and thermometer was thoroughly purged with nitrogen and then charged with 60 ml of toluene, 0.075 g (5.0×10−4 mol) of trifluoromethanesulfonic acid, 0.076 g (5.0×10−4 mol) of 1,8-diazabicyclo[5.4.0]-7-undecene, and 5.1 g (5.0×10−2 mol) of 1-hexanol, which were stirred. Further, 4.15 g (2.5×10−2 mol) of 1,1,3,3-tetramethyldisiloxane-1,3-diol was admitted into the reactor, which was evacuated to a reduced pressure of 4.7 kPa and heated at 35° C. The reactor was kept at the temperature for two hours and resumed atmospheric pressure. Composition analysis by gas chromatography revealed that 1,1,3,3-tetramethyldisiloxane-1,3-diol had completely reacted, and 1,3-dihexyloxy-1,1,3,3-tetramethyldisiloxane was produced at a selectivity of 79.1%. By-products included 1,5-dihexyloxy-1,1,3,3,5,5-hexamethyltrisiloxane and 1,7-dihexyloxy-1,1,3,3,5,5,7,7-octamethyltetrasiloxane.

Workup

customA 100-ml four-necked flask equipped with a Dimroth condenser, stirrer and thermometer
customwas thoroughly purged with nitrogen
customwas evacuated to a reduced pressure of 4.7 kPa
customhad completely reacted

Sources & evidence

ORD record: ord-440be0f6a7844653a8b021f55c53d372
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875880B2

Reaction notes

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