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

HRID 1576692Notes

Reaction equation

HRID 1576692 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

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°.

Workup

  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°

Sources & evidence

ORD record
ord-f0496fda9bca4f0ea323f0a730f12c94
Source dataset
uspto-grants-1976_09
Patent number
US03982021

Reaction notes

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