9,10-Dihydro-9,10-methanoanthracene-9-carboxaldehyde → 9,10-Dihydro-9,10-methano-9-anthracenecarboxylic acid

HRID 2198645Notes

Reaction equation

HRID 2198645 reaction equation
[CH:1]([C:3]12[CH2:17][CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=31)[C:9]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:2].CC(C)=[O:20].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.O>[CH:5]1[C:4]2[C:3]3([C:1]([OH:20])=[O:2])[CH2:17][CH:10]([C:11]4[C:16]3=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 124041419,10-Dihydro-9,10-methanoanthracene-9-carboxaldehydeHCID 131709961Jones' reagent

Product 1

HCID 125071199,10-Dihydro-9,10-methano-9-anthracenecarboxylic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 9-formyl-9,10-dihydro-9,10-methanoanthracene (3.5 g) in acetone (17 ml) was dropwise added Jones' reagent (5.0 ml) at room temperature. The reaction mixture was stirred at room temperature for 1 hour, diluted with water and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give 9,10-dihydro-9,10-methanoanthracene-9-carboxylic acid. M.P. 199.5°-200.5° C.

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-feb2041308974d5b8dda4dd5d2b4a23a
Source dataset
uspto-grants-1982_11
Patent number
US04358620

Reaction notes

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