Tetrahydrofuran → trans-5,6,7,8-Tetrahydro-1,6,7-naphthalenetriol

HRID 263321노트

반응식

HRID 263321 반응식
[O:1]1[CH:11]2[CH:2]1[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:12])[C:9]=1[CH2:10]2.[O:13]1CCCC1.Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CCOCC.O>[C:8]1([OH:12])[C:9]2[CH2:10][C@@H:11]([OH:1])[C@H:2]([OH:13])[CH2:3][C:4]=2[CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 124457371a,2,7,7a-Tetrahydronaphtho[2,3-b]oxiren-3-ol

생성물 1

HCID 12445740trans-5,6,7,8-Tetrahydro-1,6,7-naphthalenetriol

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6212Chloroform용매

실험 절차

A solution of 8.0 g. (0.048 mole) of 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol in 100 ml. of tetrahydrofuran is cooled to 0° and 20 ml. of water and 0.5 ml. of 70% perchloric acid are added. After 4 hr., a further 1.5 ml. of acid is added and the solution stirred for 16 hr. at ambient temperature and diluted with 100 ml. each of ether, 10% sodium bicarbonate and saturated salt solution. The aqueous layer is separated and washed with 150 ml. of 1:1 ether-tetrahydrofuran. The organic phase is washed with saturated salt solution, dried and evaporated to give an oil which solidifies on trituration with chloroform. Recrystallization gives in two crops, 4.85 g. of solid which is recrystallized from ethyl acetate to give 3.84 g. m.p. 179.5°-181.5°. Two further recrystallizations of a small sample give the analytical specimen, m.p. 183°-184°.

후처리

  1. additionof acid is added
  2. additionat ambient temperature and diluted with 100 ml
  3. customThe aqueous layer is separated
  4. washwashed with 150 ml
  5. washThe organic phase is washed with saturated salt solution
  6. customdried
  7. customevaporated
  8. customto give an oil which
  9. customRecrystallization
  10. customgives in two crops, 4.85 g
  11. customof solid which is recrystallized from ethyl acetate
  12. customto give 3.84 g
  13. customTwo further recrystallizations of a small sample
  14. customgive the analytical specimen, m.p. 183°-184°

출처 및 근거

ORD 기록
ord-707bbee21326442cb2c82c2e0412f233
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04156789

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