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

HRID 1779853ノート

反応式

HRID 1779853 の反応式
[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]

参加物

14

反応物 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、化合物HCID 190484163-Chloro-2-tetrahydropyranyloxy-1-propyl acetate

生成物 2

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

試薬・触媒・溶媒 3

HCID 24380Iron chloride (FeCl3)触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-cb2990a36b6e40298c03231e3950cb64
出典データセット
uspto-grants-1997_05
特許番号
US05628980

反応ノート

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