O-Xylene → HCID 54460731, compound

HRID 328539Notes

Reaction equation

HRID 328539 reaction equation
Cl[C:2](CC12CCC(C3C=CC=CC=31)C1C2=CC=CC=1)=[O:3].N1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1.[S].[H][H].[C:34]1([CH3:41])[C:35]([CH3:40])=[CH:36][CH:37]=[CH:38][CH:39]=1>[C].[Pd]>[C:34]1([CH2:41][CH:2]=[O:3])[C:35]2[CH:40]3[CH2:22][CH2:23][CH:24]([C:25]4[C:30]3=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:36]=2[CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 21415567HCID 21415567, compoundHCID 178418361HCID 178418361, compoundHCID 178527711HCID 178527711, compound

Product 1

HCID 54460731HCID 54460731, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

To a solution of 46 g of 9-(chlorocarbonylmethyl)-9,10-dihydro-9,10-ethano-anthracene in 200 ml of xylene are added 10 g of 10% palladium carbon which is contaminated with quinoline-sulphur. Then at 120° C hydrogen is passed in and after 7 hours the catalyst is filtered off and the reaction mixture evaporated in vacuo. The residue is dissolved in methylene chloride and the methylene chloride solution is extracted with sodium carbonate solution. The organic phase is isolated, dried and evaporated, to yield as residue the crude 9,10-dihydro-9,10-ethano-anthryl-acetaldehyde.

Workup

  1. customat 120° C
  2. customafter 7 hours
  3. filtrationis filtered off
  4. customthe reaction mixture evaporated in vacuo
  5. dissolutionThe residue is dissolved in methylene chloride
  6. extractionthe methylene chloride solution is extracted with sodium carbonate solution
  7. customThe organic phase is isolated
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-907eded97e474a579ef7bfeec166da98
Source dataset
uspto-grants-1977_04
Patent number
US04017542

Reaction notes

Loading…