Sulfuric Acid → Loprodiol

3,3-Bis(chloromethyl)oxetane(BCMO, 15.5 g, 0.1 mole) was added, dropwise, to a stirred, refluxing solution of 0.5 ml of concentrated sulfuric acid in 60 ml of water. The mixture was stirred under reflux for 18 hours. The mixture was cooled to 25° and then sodium carbonate (3 g) was added. When gas evolution had ceased, the mixture was extracted with ethylacetate (3×40 ml). The combined ethylacetate extracts were washed in succession with water (40 ml) and saturated sodium chloride solution (40 ml). After drying (anhydrous sodium sulfate), the solution was concentrated, in vacuo, to remove solvent. The oily, solid residue was then washed with n-heptane-methylene chloride (40 ml, 1:1, v/v) and the crystals collected by filtration. Recrystallization from small amounts of methanol gave pure 2,2-bis(chloromethyl)propane-1,3-diol, 10.8 g (69.7%), mp,75.5°-78.5° (Lit(a) mp,81°). 13C n.m.r. (PPM): 44.94(s,CH2Cl); 46.62(s, C(CH2 --)4); 61.51 (s, CH2OH).

1. temperatureunder reflux for 18 hours
2. temperatureThe mixture was cooled to 25°
3. extractionthe mixture was extracted with ethylacetate (3×40 ml)
4. washThe combined ethylacetate extracts were washed in succession with water (40 ml) and saturated sodium chloride solution (40 ml)
5. dry with materialAfter drying (anhydrous sodium sulfate)
6. concentrationthe solution was concentrated, in vacuo
7. customto remove solvent
8. washThe oily, solid residue was then washed with n-heptane-methylene chloride (40 ml, 1:1
9. filtrationv/v) and the crystals collected by filtration
10. customRecrystallization from small amounts of methanol

ORD record

ord-d52ae34ce07b45198bb9e3c7d6855b6c

Source dataset

uspto-grants-1983_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04405762