Bicyclo(2.2.1)heptan-2-one → Chroman-2-ol

HRID 2226622

Reaction equation

HRID 2226622 reaction equation
CC([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9]C=2)[C:5]=1[OH:14])=O.C1C2CC(=[O:22])C(C2)C1.N1CCCC1>C1(C)C=CC=CC=1>[O:14]1[C:5]2[C:6](=[CH:11][CH:12]=[CH:13][CH:4]=2)[CH2:7][CH2:8][CH:9]1[OH:22]

Participants

5

Reactant 3

HCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 31268PyrrolidineHCID 697331'-Hydroxy-2'-acetonaphthone

Product 1

HCID 11171070Chroman-2-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution was prepared by dissolving 10 g (0.054 mole) of 1-hydroxy-2-acetonaphthone, 6.6 g (0.06 mole) of norcamphor and 8 g (0.113 mole) of pyrrolidine in 300 cc of toluene. The solution was boiled for 10 hours and water was separated. After termination of the reaction, toluene was removed under reduced pressure, and the remaining chromanone compound was crystallized with acetone. Then, the chromanone compound was dissolved in 200 cc of methanol, and sodium boron hydride was gradually added to the solution to form a chromanol compound. Then, 7.47 g of the chromanol compound was heated at 150° to 160° C. together with 4.5 g of anhydrous copper sulfate in a carbon dioxide current for 10 minutes and the obtained viscous liquid was purified by the chromatography on silica gel to obtain 6.3 g of a chromene compound of the following formula: ##STR67##

Workup

  1. customA solution was prepared
  2. customwater was separated
  3. customAfter termination of the reaction, toluene
  4. customwas removed under reduced pressure
  5. customthe remaining chromanone compound was crystallized with acetone
  6. dissolutionThen, the chromanone compound was dissolved in 200 cc of methanol
  7. additionsodium boron hydride was gradually added to the solution

Sources & evidence

ORD record
ord-2ac70ac8780647aaaff36eb7c99770d1
Source dataset
uspto-grants-1994_09
Patent number
US05349065

Linked notes

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