2-HYDROXYMETHYL-1,3-DIOXOLANE

(66b) (a) 2-(2-Hydroxymethyl)-1, 3-dioxolane Dowex MSA-1 (90 g, carbonate form) and 2-(2-bromoethyl)-1, 3-dioxolane (18.1 g, 100 mmol) were refluxed in benzene (250 ml) for 5 hours. The resin was filtered off, washed with dichloromethane (200 ml) and methanol (500 ml). The organic solvents were evaporated and the 2-(2-hydroxyethyl)-1, 3-dioxolane distilled as a colourless oil. Yield 7.5 g (64percent). B.p. 150° C. (80 mm Hg). The structure was confirmed by 1 H NMR and 13 C NMR.Compound 5 (296 mg, 1.0 mmol) and In a four necked round-bottomed glass reactor, equipped with magnetic stirrer, thermometer, condenser maintained at -75°C (dry ice-lsopropyl alcohol) and two addition funnels, 60 g of glycol aldehyde (1.0 mol) and 62 g of ethylene glycol (1.0 mol) were loaded, followed by 10 g of 37percent HCI water solution (0.10 mol HCI) at room temperature; after 1 hour under stirring, the formation of cyclic acetal (G) was complete; the reactor was thus cooled to 0°C with an ice water bath, then a solution of 44 g (1.1 mol) of NaOH (s) and 44 ml of distilled water H2O was added in half an hour. After a slight exothermicity, at 0°C, 216 g (1.0 mmol) of (A) were slowly added. At the end of the addition, the reaction mixture was allowed to reach 20°C, and stirred for another 2 hours. The crude mixture was extracted three times with tetrahydrofuran (THF). The combined THF extracts were dehydrated with MgSO4, filtered and fractionally distilled, collecting 247 g of the partially hydrogenated ether (H) (yield 77percent mol). The aldehyde group of adduct (H) was deprotected (quantitatively) obtaining the corresponding aldehyde (J) by hydrolysis in acidic conditions (diluted HCI).In a four necked round-bottomed glass reactor, equipped with magnetic stirrer, thermometer, condenser maintained at -75°C (dry ice-lsopropyl alcohol) and two addition funnels, 60 g of glycol aldehyde (1.0 mol) and 62 g of ethylene glycol (1.0 mol) were loaded, followed by 10 g of 37percent HCI water solution (0.10 mol HCI) at room temperature; after 1 hour under stirring, the formation of cyclic acetal (G) was complete; the reactor was thus cooled to 0°C with an ice water bath, then a solution of 44 g (1.1 mol) of NaOH (s) and 44 ml of distilled water H2O was added in half an hour. After a slight exothermicity, at 0°C, 216 g (1.0 mmol) of (A) were slowly added. At the end of the addition, the reaction mixture was allowed to reach 20°C, and stirred for another 2 hours. The crude mixture was extracted three times with tetrahydrofuran (THF). The combined THF extracts were dehydrated with MgSO4, filtered and fractionally distilled, collecting 247 g of the partially hydrogenated ether (H) (yield 77percent mol). The aldehyde group of adduct (H) was deprotected (quantitatively) obtaining the corresponding aldehyde (J) by hydrolysis in acidic conditions (diluted HCI).(66b)

Molecular Weight:104.10
XLogP3:-0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:104.047344113
Monoisotopic Mass:104.047344113
Topological Polar Surface Area:38.7
Heavy Atom Count:7
Complexity:48.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes