Hydrogen Peroxide → 8-(Hexadecyloxy)-7-methoxy-1-octanol

HRID 35958Notes

Reaction equation

[CH2:1]([O:17][CH2:18][CH:19]([O:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].B.[OH-:29].[Na+].OO>O1CCCC1.O>[CH2:1]([O:17][CH2:18][CH:19]([O:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 8-(hexadecyloxy)-7-methoxy-1-octene in 100 ml of tetrahydrofuran was added a solution of 112.3 ml of 1.0M borane in tetrahydrofuran at 0° C. over a 1 hour period. The mixture was stirred on addition 3 hours at 25° C. The solution was recooled to 0° C. and a solution of 187.3 ml of 3M sodium hydroxide was slowly added followed by 216 ml of 30% hydrogen peroxide. After 30 minutes, the mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was purified by chromatography giving 20 g of the title compound as a solid.

Workup

customwas recooled to 0° C.
waitAfter 30 minutes
extractionextracted with ether
dry with materialThe ether solution was dried
customevaporated
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-633cc3b5081846cbb6054e23f6596b4f
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05411983

Reaction notes

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