Ethyl caprate → 1-Decanol

HRID 1588013Notes

Reaction equation

HRID 1588013 reaction equation
C(O[SiH](OCC)OCC)C.[C:11](OCC)(=[O:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH2:11]([OH:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 8048Ethyl caprateHCID 13830Triethoxysilane

Product 1

HCID 81741-DecanolYield 93.5%

Reagents, catalysts & solvents 1

HCID 76524Titanium tetraethoxideCatalyst

Conditions

Temperature
40 °C

Procedure

A dry Schlenk tube under argon was charged with titanium (IV) ethoxide (32 μL, 0.15 mmol) and triethoxysilane (1.39 mL, 7.5 mmol) and heated to 40° C. After 15 min., ethyl decanoate (696 μL, 3 mmol) was added. After 18 hours, the reaction was determined to be complete by GC analysis. Standard work-up afforded 444 mg (93% yield) of decanol as a clear oil.

Workup

  1. waitAfter 18 hours

Sources & evidence

ORD record
ord-fd8ecb47e30e46d99eba8cf68acc2e6b
Source dataset
uspto-grants-1993_06
Patent number
US05220020

Reaction notes

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