Trimethylolpropane → HCID 178459630, compound

Participants

Reaction Steps

To a stirred solution of trimethylolpropane (TMP) (50.0 g, 373 mmol) in acetone (1000 ml) was added p-toluene sulfonicacid (p-TSA) (1.39 g, 7.46 mmol) and 2,2-dimethylolpropane (58.2 g, 560 mmol). The reaction was stirred over night and quenched with NH4OH/ethanol (50/50 v/v) and the acetone evaporated. The crude product was dissolved in CH2Cl2 (1000 ml), extracted 3 times with water (100 ml), dried with mgSO4, and concentrated to yield a colorless oil (56.5 g, 87%). 1H NMR (CDCl3): δ0.79 (t, CH2CH3, J=7.6 Hz, 3H), 1.30 (q, CH2CH3, J=7.6 Hz, 2H), 1.38 (s, CCH3, 3H), 1.41 (s, CCH3, 3H), 2.70 (t, —OH, J=7.4 Hz, 1H), 3.54 (s, CH2OH, 2H), 3.65 (s, CH2O, 2H), 3.68 (s, CH2O, 2H). 13C NMR (CDCl3): δ7.00 (s, CH2CH3, 1C), 20.17 (s, CH2CH3, 1C), 23.74 (s, CCH3, 1C), 27.30 (s, CCH3, 1C), 36.91 (s, C(CH2)4, 1C), 62.51 (s, CH2OH, 1C), 65.15 (s, CH2O, 2C), 98.16 (s C(CH3)2, 1C).

Provenance & Evidence