Potassium Hydroxide → NSC245059

HRID 567648Notes

Reaction equation

HRID 567648 reaction equation
C([O:4][CH:5]1[CH2:14][CH:13]2[CH2:15][CH:6]1[CH:7]1[CH:12]2[CH:11]2[CH2:16][CH:8]1[CH:9]=[CH:10]2)(=O)C.O1CCOCC1.[OH-].[K+].O.O.C(O)(=O)C(O)=O>O>[OH:4][CH:5]1[CH2:14][CH:13]2[CH2:15][CH:6]1[CH:7]1[CH:12]2[CH:11]2[CH2:16][CH:8]1[CH:9]=[CH:10]2

Participants

6

Reactant 4

HCID 14797Potassium Hydroxide2×HCID 312751,4-DioxaneHCID 61373Oxalic acid dihydrateHCID 2694431,2,3,4,4a,5,8,8a-Octahydro-1,4:5,8-dimethanonaphthalen-2-yl acetate

Product 1

HCID 428925NSC245059Yield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 parts of 8-acetoxytetracyclo[4.4.0.12,5.17,10]dodec-3-ene, 200 parts of 1,4-dioxane, 50 parts of distilled water, and 50 parts of potassium hydroxide were placed in a flask. A hydrolysis reaction was carried out for 4 hours in a nitrogen atmosphere at 100° C. After cooling, an aqueous solution of oxalic acid di-hydrate in an amount of 1.1 equivalent of the potassium hydroxide was added dropwise to coagulate the reaction product. The coagulate was washed with a large amount of water, then washed with a small amount of toluene, and dried to obtain 8-hydroxytetracyclo [4.4.0.12,5.17,10]dodec-3-ene of the following formula (14) at an yield of 95%.

Workup

  1. customA hydrolysis reaction
  2. temperatureAfter cooling
  3. washThe coagulate was washed with a large amount of water
  4. washwashed with a small amount of toluene
  5. customdried

Sources & evidence

ORD record
ord-22d0014651f947c4a34c59419dedbfa1
Source dataset
uspto-grants-2001_01
Patent number
US06180316B2

Reaction notes

Loading…