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

HRID 437045

Reaction equation

HRID 437045 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.Cl(O)(=O)(=O)=[O:15].C(Cl)(Cl)Cl>O1CCCC1.CCOCC.C(=O)(O)[O-].[Na+]>[C:8]1([OH:12])[C:9]2[CH2:10][C@@H:11]([OH:1])[C@H:2]([OH:15])[CH2:3][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 24247Perchloric AcidHCID 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 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 8.0 g of 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol in 100 ml of tetrahydrofuran is cooled to 0° C. and 20 ml of water and 0.5 ml of 70% perchloric acid are added. After 4 hours, a further 1.5 ml of acid is added and the solution is stirred for 16 hours 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, melting point 179.5°-181.5° C. Two further recrystallizations of a small sample give the analytical specimen, melting point 183°-184° C.

Workup

  1. customThe aqueous layer is separated
  2. washwashed with 150 ml of 1:1 ether-tetrahydrofuran
  3. washThe organic phase is washed with saturated salt solution
  4. customdried
  5. customevaporated
  6. customto give an oil which
  7. customRecrystallization

Sources & evidence

ORD record
ord-1f98cbea66f64b34b71df0b5498e18ea
Source dataset
uspto-grants-1977_06
Patent number
US04029676

Linked notes

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