m-Chloroperbenzoic acid → 2,3-Epoxypropyl 6,7-epoxy-5,6,7,8-tetrahydro-1-naphthyl ether

HRID 1581072

反応式

HRID 1581072 の反応式
[O:1]1[CH2:15][CH:2]1[CH2:3][O:4][C:5]1[C:14]2[CH2:13][CH:12]=[CH:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[O:24]1[CH:12]2[CH:11]1[CH2:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([O:4][CH2:3][CH:2]3[O:1][CH2:15]3)[C:14]=1[CH2:13]2

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 110526861-(2,3-Epoxypropoxy)-5,8-dihydronaphthalene

生成物 1

HCID 124457662,3-Epoxypropyl 6,7-epoxy-5,6,7,8-tetrahydro-1-naphthyl ether

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a well-stirred solution of 7 g. (0.03 m.) of 1-(2,3-epoxy-propoxy)-5,8-dihydro-naphthalene (prepared as described in application Ser. No. 768,176, filed Oct. 16, 1968, issued Oct. 13, 1970, as U.S. Pat. No. 3,534,085) in 60 ml. of CH2Cl2, 7.1 g. (0.03 m.) of 85% m-chloroperbenzoic acid in 100 ml. CH2Cl2 is added dropwise at such a rate that the temperature is maintained between 25° to 30° C. The mixture is stirred overnight at room temperature. The resulting precipitate (m-chlorobenzoic acid) is filtered off and the CH2Cl2 extract is washed successively with sat. NaHCO3 solution, and water. After drying (MgSO4), the solution is evaporated in vacuo to give 7.2 g. (95%) of oil which solidifies. A sample recrystallized from ether gives white needles, m.p. 85°-87°; λ Nujolmax 1330-1350 cm-1 (epoxy), τ CDCl3 absence of vinyl protons 4.0-4.2 region.

後処理

  1. temperatureis maintained between 25° to 30° C
  2. filtrationThe resulting precipitate (m-chlorobenzoic acid) is filtered off
  3. extractionthe CH2Cl2 extract
  4. washis washed successively with sat. NaHCO3 solution, and water
  5. dry with materialAfter drying (MgSO4)
  6. customthe solution is evaporated in vacuo
  7. customto give 7.2 g
  8. customA sample recrystallized from ether
  9. customgives white needles, m.p. 85°-87°

出典と根拠

ORDレコード
ord-b7f31ff26b7a4157844d820b3400ddbd
出典データセット
uspto-grants-1976_01
特許番号
US03935267

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