Acetate → 147331-60-0

HRID 1581077Notes

Reaction equation

HRID 1581077 reaction equation
[C:1]1([OH:11])[C:10]2CC=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O[C:16](=[O:18])[CH3:17])(=O)C.C([O-])(=[O:21])C.II>C([O-])(=O)C.[Ag+].O.C(O)(=O)C.N1C=CC=CC=1>[C:16]1([OH:18])[C:17]2[CH2:10][C@H:1]([OH:11])[C@H:2]([OH:21])[CH2:3][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 175AcetateHCID 807IodineHCID 7918Acetic AnhydrideHCID 974665,8-Dihydro-1-naphthol

Product 1

HCID 51656356147331-60-0

Reagents, catalysts & solvents 4

HCID 11246Silver acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 29.2 g. (0.2 mole) of 5,8-dihydro-1-naphthol and 40 ml. of acetic anhydride in 100 ml. of pyridine is prepared. After 16 hr. the solvent is removed in vacuo and the residue dissolved in ether and washed with 200 ml. of 5% hydrochloric acid, water, 200 ml. of 10% sodium hydroxide, saturated salt solution and dried. Solvent removal gives 34.2 g. (90.5%) of crude acetate which is dissolved in 900 ml. of acetic acid and 36 ml. of water. 53.3 g. (0.32 mole) of silver acetate is added followed by 40.6 g. (0.16 g-atom) of iodine. The slurry is heated with good stirring at 85°± 10° for 3 hr. under nitrogen, cooled and filtered. The filtrate is evaporated in vacuo and the residue dissolved in 250 ml. of methanol and cooled to 0°. A solution of 40 g. of sodium hydroxide in 200 ml. of water is added under nitrogen and the mixture stirred overnight. The bulk of the methanol is removed in vacuo whereupon a solid forms. The solid is separated by filtration, dissolved in 150 ml. of water and acidified with 20 ml. of concentrated hydrochloric acid. Cooling gives a solid which is filtered and dried to give 16.5 g. 2,3 cis-5,6,7,8-tetrahydro-1,6,7-naphthalenetriol) m.p. 184.5°-187°. Three recrystallizations from absolute ethanol give the analytical sample, m.p. 188°-188.5°.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionthe residue dissolved in ether
  3. washwashed with 200 ml
  4. dry with materialof 10% sodium hydroxide, saturated salt solution and dried
  5. customSolvent removal
  6. customgives 34.2 g
  7. temperatureThe slurry is heated
  8. temperatureunder nitrogen, cooled
  9. filtrationfiltered
  10. customThe filtrate is evaporated in vacuo
  11. dissolutionthe residue dissolved in 250 ml
  12. temperatureof methanol and cooled to 0°
  13. additionof water is added under nitrogen
  14. stirringthe mixture stirred overnight
  15. customThe bulk of the methanol is removed in vacuo whereupon a solid forms
  16. customThe solid is separated by filtration
  17. dissolutiondissolved in 150 ml
  18. temperatureCooling
  19. customgives a solid which
  20. filtrationis filtered
  21. customdried
  22. customto give 16.5 g
  23. customThree recrystallizations from absolute ethanol
  24. customgive the analytical sample, m.p. 188°-188.5°

Sources & evidence

ORD record
ord-1cbaae1e195d4e35a0e4c0b0cb2a635b
Source dataset
uspto-grants-1976_01
Patent number
US03935267

Reaction notes

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