p-Toluenesulfonic acid → 2-Propanol, 1-chloro-3-[(tetrahydro-2H-pyran-2-yl)oxy]-

HRID 977792

반응식

HRID 977792 반응식
[OH:1][CH2:2][CH:3]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[CH2:4][Cl:5].[CH2:13](C1OC1)[Cl:14].C(OCC(O)CCl)(=O)C.C(OC(CCl)CO)(=O)C.O1C=CCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC(OC1CCCCO1)CCl)(=O)C.O1CCCCC1OCC(OC(=O)C)CCl.C(=O)([O-])[O-].[K+].[K+]>[Fe](Cl)(Cl)Cl.CO.C(O)(=O)C>[OH:1][CH2:2][CH:3]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[CH2:4][Cl:5].[O:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[O:6][CH2:3][CH:2]([OH:1])[CH2:13][Cl:14]

참가 물질

14

반응물 9

HCID 6101p-Toluenesulfonic acidHCID 7835EpichlorohydrinHCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 980693-Chloro-2-hydroxypropyl acetateHCID 136667621-Hydroxy-2-(tetrahydropyran-2-yl)oxy-3-chloropropaneHCID 159164011-Chloro-3-hydroxypropan-2-yl acetateHCID 19048387HCID 19048387, 화합물HCID 19048416HCID 19048416, 화합물

생성물 2

HCID 113214982-Propanol, 1-chloro-3-[(tetrahydro-2H-pyran-2-yl)oxy]-HCID 136667621-Hydroxy-2-(tetrahydropyran-2-yl)oxy-3-chloropropane

시약·촉매·용매 3

HCID 24380Iron chloride (FeCl3)촉매HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

1-hydroxy-2-(tetrahydropyran-2-yl)oxy-3-chloropropane can be prepared by the following scheme: epichlorohydrin is reacted with acetic acid in the presence of a catalytic amount of iron trichloride to give a mixture of 1-acetyloxy-3-chloropropan-2-ol and 2-acetyloxy-3-chloropropan-1-ol, the major component. The mixture is treated with dihydropyran in the presence of p-toluenesulfonic acid for five hours at 25° C. to give a mixture of 1-acetyloxy-2-(tetrahydropyran-2-yl)oxy-3-chloropropane and 1-(tetrahydropyranyloxy)-2-acetyloxy-3-chloropropane. The mixture is added to a rapidly stirred mixture of aqueous methanol and potassium carbonate at 25° C. and stirred for two hours. Evaporation of the methanol, extraction and drying yields a mixture 1-hydroxy-2-(tetrahydropyran-2-yl)oxy-3-chloropropane and 1-(tetrahydropyran-2-yl)oxy-2-hydroxy-3-chloropropane. Fractional vacuum distillation yields pure 1-hydroxy-2-(tetrahydropyran-2-yl)-oxy-3-chloro-propane since the minor impurity is converted into the more volatile epoxy compound during the distillation procedure.

후처리

  1. customto give
  2. customto give
  3. customEvaporation of the methanol, extraction
  4. customdrying

출처 및 근거

ORD 기록
ord-b4654c1742964587b06371c1c348a591
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614638

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