Tetraethylene Glycol → HCID 86639481, compound

HRID 74127Notes

Reaction equation

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

Participants

Conditions

Temperature: 200 °C

Procedure

2-Methylundecanal (4.61 g, 5.55 ml, 0.025 mol), tetraethylene glycol (97.1 g, 86.3 ml, 0.5 mol) and 10% Pd/C (0.3 g, 6.5 wt % to n-decanal) are charged to a 150 ml Parr reactor. The system is purged with nitrogen three times. Then 500 psi of hydrogen is charged, the reactor is heated to 200° C., and the hydrogen pressure is adjusted to 1000 psi. After 3 hours at 200° C. and 1000 psi, GC analysis shows 99.5% conversion of 2-methyl-undecanal and detect 11-methyl-3,6,9,12-tetraoxa-1-tricosanol (82.3%) and 2-methyundecanol (7.9%).

Workup

customThe system is purged with nitrogen three times
additionThen 500 psi of hydrogen is charged

Sources & evidence

ORD record: ord-490e184a63114026ad17af13d635aad8
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829229B2

Reaction notes

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