HCID 21415567, compound → HCID 21415565, compound

HRID 328538Notes

Reaction equation

HRID 328538 reaction equation
[N:1]1C2C(=CC=CC=2)C=C[CH:2]=1.[S].Cl[C:13]([CH2:15][C:16]12[CH2:31][CH2:30][CH:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=31)[C:22]1[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:14].[H][H]>[Pd].C1(C)C(C)=CC=CC=1>[OH:14][CH:13]([C:2]#[N:1])[CH2:15][C:16]12[CH2:31][CH2:30][CH:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=31)[C:22]1[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 21415567HCID 21415567, compoundHCID 178418361HCID 178418361, compoundHCID 178527711HCID 178527711, compound

Product 1

HCID 21415565HCID 21415565, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

10 g of 10% strength palladium on charcoal, poisoned with quinoline-sulphur, are added to a solution of 46 g of 9 -(chlorocarbonylmethyl)-9,10-dihydro-9,10-ethano-anthracene in 200 ml of xylene, and hydrogen is then passed through the mixture at 120° C. After 7 hours, the catalyst is filtered off and the filtrate is evaporated in vacuo. The residue is dissolved in methylene chloride and extracted by shaking with sodium carbonate solution. The organic phase is separated off, dried over sodium sulphate and then diluted to a volume of 250 ml by adding methylene chloride. After 1 ml of triethylamine has been added, 20 ml of hydrogen cyanide are added and the mixture is left to stand for 12 hours at room temperature. It is then extracted by shaking with water and the solvent is evaporated. Crystalline 9-(2-hydroxy-2-cyano-ethyl)-9,10-dihydro-9,10-ethano-anthracene is obtained as the residue and after recrystallisation from methylene chloride-petroleum ether has a melting point of 139°-141° C.

Workup

  1. customis then passed through the mixture at 120° C
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is evaporated in vacuo
  4. dissolutionThe residue is dissolved in methylene chloride
  5. extractionextracted
  6. customThe organic phase is separated off
  7. dry with materialdried over sodium sulphate
  8. additiondiluted to a volume of 250 ml
  9. additionby adding methylene chloride
  10. additionAfter 1 ml of triethylamine has been added
  11. addition20 ml of hydrogen cyanide are added
  12. waitthe mixture is left
  13. waitto stand for 12 hours at room temperature
  14. extractionIt is then extracted
  15. stirringby shaking with water
  16. customthe solvent is evaporated

Sources & evidence

ORD record
ord-f2b26bcdced849a2b65d00c034ebbe7a
Source dataset
uspto-grants-1977_04
Patent number
US04017542

Reaction notes

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