Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Preparation of α,ω-Diols of Long Carbon Chains and Their Use in Polyurethane Synthesis
Kohtaro OsakadaYasumasa TakenakaIsao YamaguchiTakakazu Yamamoto
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1998 Volume 71 Issue 6 Pages 1477-1482


NaH promoted coupling reaction of HO(CH2)12O–TBDMS (1, TBDMS=SiMe2(t-Bu)) and Br(CH2)12O–TBDMS (2) followed by deprotection of the organosilyl groups affords HO(CH2)12O(CH2)12OH (5). 1,12-Dodecanediol reacts with an excess amount of 2 in the presence of NaH to give TBDMS–O(CH2)12O(CH2)12O(CH2)12O–TBDMS (6) which is turned into HO(CH2)12O(CH2)12O(CH2)12OH (7) by removal of the protecting groups. Similar 1 : 2 condensation of hydroquinone with 2 and with Br(CH2)6O–TBDMS (3) leads to formation of the corresponding α,ω-diols, HO(CH2)12OC6H4O(CH2)12OH (9) and HO(CH2)6OC6H4O(CH2)6OH (11), respectively. The four new long α,ω-diols are isolated and characterized by means of IR and NMR spectroscopy as well as elemental analyses. Polyaddition reactions of 5, 7, 9, and 11 to 1,3-bis(isocyanatomethyl)benzene and 1,1′-methylenebis[4-isocyanatobenzene] give the corresponding poly(urethane)s in high yields. The obtained polymers, which were characterized by IR and NMR spectroscopy, have molecular weights over 20000 as determined from gel permeation chromatography using polystyrene standards.

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