(-)-3-Hydroxytetrahydrofuran
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(-)-3-Hydroxytetrahydrofuran
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CAS No:
86087-24-3
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Formula:
C4H8O2
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Chemical Name:
(-)-3-Hydroxytetrahydrofuran
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Synonyms:
3-Furanol,tetrahydro-,(3R)-;3-Furanol,tetrahydro-,(R)-;(3R)-Tetrahydro-3-furanol;(R)-Tetrahydro-3-furanol;(-)-3-Hydroxytetrahydrofuran;(R)-(-)-3-Hydroxytetrahydrofuran;(R)-3-Hydroxytetrahydrofuran;3(R)-Hydroxytetrahydrofuran;(R)-Tetrahydrofuran-3-ol;(3R)-3-Hydroxytetrahydrofuran;(R)-(-)-Tetrahydrofuran-3-ol;(R)-(-)-Tetrahydrofuran-3-ol;(3R)-Tetrahydrofuran-3-ol;(3R)-Oxolan-3-ol;(3R)-Oxolan-3-ol;(R)-3-Hydroxytetrahydrofuran;(r)-(-)-3-Hydroxytetrahydrofuran;3-Furanol tetrahydro-,(3R)-
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CAS No:
Safety Information
NA 1993 / PGIII
3
R36/37/38
S26-S36
Xi:Irritant;
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 41 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
(-)-3-Hydroxytetrahydrofuran Use and Manufacturing
800 mL of toluene was added to 218 g (1.758 mol) of (No.)-4-chloro-l, 3-butanediol prepared in Example 3, and stirring was performed for 16 hours under reflux. The reaction mixture was cooled to room temperature and, after adding 37.3 g (0.352 mol) of NaDilute hydrochloric acid (17.5 ml of conc. hydrochloric acid diluted with 332.50 ml of water) was added to (R)-4-chloro-1, 3-butanediol (175 g) and stirring was performed for 2 hours under reflux. After completion of the reaction monitored by gas chromatography, the reaction mixture was cooled to 0 to 5°C followed by a pH adjustment between 7 to 8 by using aqueous sodium hydroxide solution (82.5 g of sodium hydroxide dissolved in 165 ml of water). The resulting reaction mass was diluted with methanol (525 ml) followed by distillation under reduced pressure maintaining temperature below 45°C. Water was completely removed using methanol stripping (2 x 525 ml) followed by addition of methyl tert-butyl ether (525 ml) to the concentrated mass. The resulting suspension was stirred for 30 minutes followed by filtration to remove inorganic materials. The solid cake was washed with methyl tert-butyl ether (100 ml) followed by distillation under reduced pressure maintaining temperature below 40°C to obtain a crude oil (88.46 g). The resulting crude material was distilled under reduced pressure at 90 to 95°C (5 mmHg pressure) to give pure (R)-tetrahydrofuran-3-ol as an oil (73.62 g, 59.47 percent).1H-NMR: (400 MHz, CDC13): ö: 4.44-4.45 (m, 1H), 3.90-3.97 (m, 1H), 3.69-3.80 (m, 2H), 3.02-3. 12 (brs, 1H), 2.00-2.08 (m, 1H), 1.84-2.00 (m, 1H)Mass [M+Hj: 88.81 Purity by GC: 99.43percent areaSpecific optical Rotation (C= 1, Methanol): -17.57°5 g of the catalyst used in was loaded into a completely automated continuous fixed-bed reactor made of 316 stainless steel, after which the internal temperature of the reactor was adjusted to 100°C and then a dioxane solution containing 10 wtpercent of (R)- 1, 2, 4- butanetriol (optical purity of 99.0percent) was fed into the reactor at a WHSV of 2.0 hEXAMPLE 4
Computed Properties
Molecular Weight:88.11
XLogP3:-0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:88.052429494
Monoisotopic Mass:88.052429494
Topological Polar Surface Area:29.5
Heavy Atom Count:6
Complexity:44.8
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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