1003-85-6|5,5-Dimethyl-1,3,2-dioxathiane 2-oxide| Ambeed

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Quality Control of [ 1003-85-6 ] Purity: 95% SDS Specification

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Product Details of [ 1003-85-6 ]

CAS No. :	1003-85-6
Formula :	C₅H₁₀O₃S
M.W :	150.20
SMILES Code :	O=S1OCC(C)(C)CO1
MDL No. :	MFCD25954041
InChI Key :	MBWNQWVADQDHDU-UHFFFAOYSA-N
Pubchem ID :	10877294

Safety of [ 1003-85-6 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H315-H318-H317
Precautionary Statements:	P261-P264-P280-P362+P364-P333+P313-P305+P351+P338+P310
Class:	8
UN#:	1760
Packing Group:	Ⅲ

Application In Synthesis of [ 1003-85-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1003-85-6 ]

[ 1003-85-6 ] Synthesis Path-Downstream 1~35

1
[ 1003-85-6 ]
[ 60-29-7 ]
phenylmagnesium bromide [ No CAS ]
[ 92-52-4 ]
[ 40894-00-6 ]
[ 945-51-7 ]

References: [1]Journal of the American Chemical Society,1956,vol. 78,p. 454,457.

2
[ 126-30-7 ]
[ 1003-85-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With thionyl chloride; In dichloromethane; water;	EXAMPLE 1 Production of 5.5-dimethyl -1,3,2-dioxathiane-2-oxide 25.36 g (0.24 mol) of 2,2-dimethylpropane-1,3-diol was suspended at room temperature in 150 ml of methylene chloride in a 500 ml three-necked flask. 37.36 g (0.31 mol) of thionyl chloride was instilled over 30 minutes. After the end of the addition, the reaction solution was held at reflux for 1.5 hours and then cooled to room temperature. 100 ml of water was added to the reaction. The aqueous phase was discarded; the organic phase was extracted three times with saturated NaHCO3 solution (100 ml), then dried with Na2 SO4 and concentrated by evaporation on a rotary evaporator. The residue was distilled at 24 mbars and 78 C. The product was a pure colorless liquid according to GC and weighed 23.4 g, which corresponded to a yield of 92 percent.
	With thionyl chloride; at 20 - 111℃; for 6.0h;Heating / reflux;Product distribution / selectivity;	A 250 ml four-neck stirred apparatus with condenser, bubble counter, dropping funnel, thermometer and blade stirrer was initially charged with 31.20 g (0.30 mol) of 2,2-dimethyl-1,3-propanediol (neopentyl glycol) at room temperature and heated to 80 C. in an oil bath. Thionyl chloride was then added dropwise with stirring to the solid reactant. The reaction commenced immediately, which was shown by the vigorous evolution of gas. In the course of this, the internal temperature rose to 85 C. and the solid 2,2-dimethyl-1,3-propanediol began to be converted to a liquid. After addition of about 44.6 g (0.375 mol) of thionyl chloride within one hour, in spite of further dropwise addition of thionyl chloride, no further evolution of gas was observed. The internal temperature was then raised to 100 C. and further thionyl chloride was added dropwise up to a total amount of 89.25 g (0.75 mol) and a total dropwise addition time of about 2 hours, in the course of which still no further evolution of gas took place. The mixture was then stirred at an oil bath temperature of 130 C. for 3 hours, in the course of which the mixture refluxed at an internal temperature of about 111 C. Subsequently, the mixture was cooled to room temperature and analyzed by gas chromatography. It was not possible to detect any 1,3-dichloro-2,2-dimethylpropane, but rather mainly the cyclic ester formed from the diol and thionyl chloride.
535 mg	With thionyl chloride; In dichloromethane; at 40℃; for 3.0h;Cooling with ice;	Step 1: 5,5-Dimethyl-[1,3,2]dioxathiane 2-oxide Thionylchloride (735 mL) is added to a solution of 2,2-dimethylpropane-1,3-diol (1 g) in dichloromethane (10 mL) chilled in an ice bath. The mixture is heated to 40 C. for 3 hours and partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The organic phase is washed with brine, dried (MgSO4) and concentrated to give the title compound. Yield: 535 mg; TLC: rf=0.65 (silicagel, cyclohexane/ethyl acetate 3:1).

535 mg	With thionyl chloride; In dichloromethane; at 40℃; for 3.0h;Cooling with ice;	Thionylchloride (735 mL) is added to a solution of 2, 2-dimethylpropane-1 ,3-diol (1 g) in dichloromethane (10 mL) chilled in an ice bath. The mixture is heated to 40C for 3 hou rs and partitioned between satu rated aq ueous NaHCO3 solution and dichloromethane. The organic phase is wahed with brine, dried (MgSO4) and concentrated to give the title compound. Yield: 535 mg; TLC: rf = 0.65 (silicagel, cyclohexane/ethyl acetate 3:1 ).
535 mg	With thionyl chloride; In dichloromethane; at 40℃; for 3.0h;Cooling with ice;	Thionylchloride (735 mL) is added to a solution of 2, 2-dimethylpropane-1 ,3-diol (1 g) in dichloromethane (10 mL) chilled in an ice bath. The mixture is heated to 40C for 3 hou rs and partitioned between satu rated aq ueou s N a H CO3 solution and dichloromethane. The organic phase is wahed with brine, dried (MgSO4) and concentrated to give the title compound. Yield: 535 mg; TLC: rf = 0.65 (silicagel, cyclohexane/ethyl acetate 3:1 ).
	With thionyl chloride; In dichloromethane;	EXAMPLE 1 104.15 g of 2.2-dimethyl-1,3-propanediol (1 mol) are suspended in 200 ml of methylene chloride in a 500 ml four-necked flask which is provided with a stirrer, a reflux condenser, a thermometer and a dropping funnel. 125 g (1.05 mol) of thionyl chloride are added dropwise within 1 hour while stirring at 5-10 C. The reaction mixture is then warmed to 40 C. for 3 hours. The thus obtained oil is washed with 50 ml of water and then with 50 ml of NaHCO3 solution and dried over Na2 SO4. After removing the majority of methylene chloride on a rotary evaporator the residue is distilled at 85-87 C./30 mmHg over a 10 cm isolated column filled with Raschig rings. There are obtained 142.5 g of 5,5-dimethyl-1,3,2-dioxathiane 2-oxide in the form of a colourless oil.

References: [1]Synthetic Communications,1997,vol. 27,p. 701 - 707.
[2]Tetrahedron Letters,1990,vol. 31,p. 2975 - 2978.
[3]Patent: US5159100,1992,A .
[4]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 6721 - 6727,7.
[5]European Journal of Medicinal Chemistry,2011,vol. 46,p. 907 - 913.
[6]Journal of the American Chemical Society,1949,vol. 71,p. 2031,2034.
[7]Justus Liebigs Annalen der Chemie,1970,vol. 737,p. 144 - 151.
[8]Bulletin de la Societe Chimique de France,1961,p. 1495 - 1498.
[9]Bulletin de la Societe Chimique de France,1961,p. 1495 - 1498.
[10]Australian Journal of Chemistry,1977,vol. 30,p. 569 - 578.
[11]Patent: US2008/228016,2008,A1 .Location in patent: Page/Page column 4-5.
[12]Patent: US2013/252937,2013,A1 .Location in patent: Paragraph 0474.
[13]Patent: WO2013/144097,2013,A1 .Location in patent: Page/Page column 85.
[14]Patent: WO2013/144098,2013,A1 .Location in patent: Page/Page column 137.
[15]Patent: US4596879,1986,A .

3
[ 1003-85-6 ]
[ 1755-97-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hypochlorite;ruthenium trichloride; In dichloromethane; water; isopropyl alcohol;	(b) with sodium hypochlorite: 10.0 g (0.064 mol) of 5,5-dimethyl-1,3,2-dioxathiane-2-oxide was introduced at 20 C. in 100 ml of methylene chloride and 50 ml of water in a 250 ml three-necked flask. 0.02 g of 90 percent ruthenium trichloride was added as a catalyst. 152.45 g (0.0727 mol) of sodium hypochlorite in water was added with stirring for 20 minutes, and the temperature increased to 30 C. The reaction mixture was stirred for five more hours and mixed with 10 drops of isopropanol; the yellow color faded and a black precipitate formed. The water phase was extracted twice with methylene chloride (50 ml), and the combined organic phases were extracted with NaHCO3 solution (100 ml), dried with Na2 SO4 and concentrated by evaporation. The white crystalline product was dried overnight at room temperature at a pressure of 15 mbars and weighed 10.65 g, which corresponded to a yield of 99 percent, relative to the 5,5-dimethyl-1,3,2-dioxathiane-2-oxide used.

References: [1]Patent: US5159100,1992,A .
[2]Tetrahedron,1964,vol. 20,p. 2781 - 2795.
[3]Bulletin de la Societe Chimique de France,1961,p. 1495 - 1498.
[4]Australian Journal of Chemistry,1977,vol. 30,p. 569 - 578.
[5]Journal of the Chemical Society,1960,p. 201 - 211.
[6]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 6721 - 6727,7.

4
[ 1003-85-6 ]
[ 143-33-9 ]
[ 103804-80-4 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 2975 - 2978.

7
[ 1003-85-6 ]
[ 357166-76-8 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 2975 - 2978.

8
[ 1003-85-6 ]
[ 129415-93-6 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 2975 - 2978.

9
[ 1003-85-6 ]
[ 129415-94-7 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 2975 - 2978.

10
[ 1003-85-6 ]
(E)-6-Bromo-5,5-dimethyl-hex-2-enenitrile [ No CAS ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 2975 - 2978.

11
[ 1003-85-6 ]
[ 129415-86-7 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 2975 - 2978.

12
[ 1003-85-6 ]
[ 129415-92-5 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 2975 - 2978.

13
[ 773837-37-9 ]
[ 1003-85-6 ]
[ 103804-80-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; dimethyl sulfoxide;	EXAMPLE 2 30 g (0.198 mol) of 5,5-dimethyl-1,3,2-dioxathiane 2-oxide (prepared in accordance with Example 1) and 15.5 g (0.317 mol) of dry, finely powdered NaCN in 40 ml of dry dimethyl sulphoxide are added while gassing with argon to a 350 ml four-necked flask which is provided with a stirrer, a reflux condenser and a thermometer. The reaction mixture is stirred at 100 C. for 30-36 hours. The majority of the dimethyl sulphoxide (35-36 ml) is then distilled off cautiously at 65-70 C./3 mmHg over a 5 cm Vigreux column. The residue is suspended in 130 ml of water and the suspension is brought to pH 3 with about 16 ml of 25% HCl solution. The black mixture is extracted continuously with 80 ml of isopropyl ether. After drying over Na2 SOt4 and removing the solvent on a rotary evaporator the product is distilled over a 5 cm Vigreux column at 75-82 C./0.2 mmHg. There are obtained 16 g of 4-hydroxy-3,3-dimethyl-butyronitrile in the form of an oil.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 907 - 913.
[2]Patent: US4596879,1986,A .

14
[ 1003-85-6 ]
C₂₃H₂₀ClNO₃ [ No CAS ]