ChemicalBook CAS DataBase List 1,1-Bis(hydroxymethyl)cyclopropane

1,1-Bis(hydroxymethyl)cyclopropane synthesis

7synthesis methods

Product Name:1,1-Bis(hydroxymethyl)cyclopropane
CAS Number:39590-81-3
Molecular formula:C5H10O2
Molecular Weight:102.13

1559-02-0
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39590-81-3
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Yield:39590-81-3 81 g (0.79 mol, 84%)

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran

Steps:

17.7 Step 7
Step 7 1,1-cyclopropanedimethanol A solution of lithium aluminum hydride (50 g, 1.32 mol) in 1.6L of THF was cooled to -18° C. under N₂. A solution of diethyl 1,1-cyclopropanedicarboxylate (175 g, 0.94 mol) in 1.2L of THF was then added dropwise over 50 min, at such a rate that the internal temperature of the reaction remained below 10° C. The cooling bath was then removed, and after 15 min, the temperature had reached 15° C. The reaction was then quenched by careful addition of 50 mL H₂ O, followed by 50 mL of 15% NaOH, and then 150 mL of H₂ O. After the mixture turned white, it was filtered through celite, and the bed was washed with 4L of THF. Evaporation gave an oil which was distilled to give 81 g (0.79 mol, 84%) of the title compound as a colorless oil, b.p. 131°-138° C./15 mm Hg. ¹ H NMR (CDCl₃) δ0.48 (4H, s), 3.30 (2H, s), 3.58 (4H, s).

References:

Merck Frosst Canada, Inc. US5212180, 1993, A

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