[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:6]([OH:18])[CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17].C(O)COCCOCCOCCOCCCC>[Pd].C(O)CCC>[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:16]([OH:17])[CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][OH:18]n-Butyraldehyde (1.8 g, 2.25 ml; 0.025 mol), tetraethylene glycol (97.1 g, 86.3 ml; 0.5 mol), and 0.09 g of 10% Pd/C 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 180° C., and set 1000 psi of hydrogen. After 4 hrs at 180° C. and 1000 psi n-butyraldehyde reacts completely, and GC analysis shows formation of 3,6,9,12-tetraoxahexadecanol (91.2%), n-butanol (4.8%) and 5,8,11,14,17-pentaoxauneicosane (1.1%).
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