Pentaerythritol → (1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanol

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Pentaerythritol (60 g, 440.7 mmol) was added to a stirring solution of dioctyl phthalate (100 mL) containing trace p-toluene sulfonic acid monohydrate, and heated to 120° C. After triethyl orthoacetate (71.685 g, 81 mL, 441.87 mmol) was added in one portion the reaction was equipped with a distillation apparatus and stirred for 22 h. Upon return, 64 mL of ethanol had distilled (83% of the theoretical amount). TEA (40 drops) was added, stirred for 10 minutes, heated to 160° C. The TEA and remaining ethanol were removed under vacuum. After changing the distillation glassware, the final product, a white solid, was isolated by vacuum distillation at 185° C. and recrystallized using benzene. Yield: 83%, 58.64 g. 1H NMR (CDCl3; 500 MHz) δ ppm: 1.453 (s, 3H, CH3), 1.58 (t, 1H, OH), 3.454 (d, 2H, CCH2OH), and 4.015 (s, 6H, OCH2C). 13C NMR (CDCl3; 125.8 MHz) δ ppm: 23.53 (CH3), 35.71 (CH2CCH2), 61.50 (CCH2OH), 69.41 (OCH2C), and 108.67 (OCCH3). ESI-MS (m/z): 161.06 (161.07 calc'd for C7H12O4 [M+H]+). Elemental analysis calc'd (found) for C7H12O4: C, 52.49 (51.58); H, 7.55 (7.67).

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