Hydrochloric Acid → HCID 86744454, compound

HRID 1111551Notes

Reaction equation

HRID 1111551 reaction equation
[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([C:15]3[CH:24]=[CH:23][C:22]4[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=4[CH:16]=3)=O)=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:29]([C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([C:42]([C:44]3[CH:53]=[CH:52][C:51]4[C:50]([CH3:55])([CH3:54])[CH2:49][CH2:48][C:47]([CH3:57])([CH3:56])[C:46]=4[CH:45]=3)=O)[CH:38]=2)[C:33]=1[CH2:58][CH3:59])(=[O:31])=[O:30])[CH3:2].Cl>C(O)(=O)C.C(Cl)Cl.[Zn]>[CH2:1]([C:3]1[C:12]2[CH:11]=[CH:10][C:9](=[CH:13][C:15]3[CH:24]=[CH:23][C:22]4[C:21]([CH3:25])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:27])([CH3:28])[C:17]=4[CH:16]=3)[CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[S:29]([C:32]1[CH:41]=[CH:40][C:39]2[CH2:38][C:37](=[CH:42][C:44]3[CH:53]=[CH:52][C:51]4[C:50]([CH3:55])([CH3:54])[CH2:49][CH2:48][C:47]([CH3:57])([CH3:56])[C:46]=4[CH:45]=3)[CH:36]=[CH:35][C:34]=2[C:33]=1[CH2:58][CH3:59])(=[O:31])=[O:30])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric Acid3×HCID 86744452HCID 86744452, compound

Product 1

HCID 86744454HCID 86744454, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of 0.50 g of ethyl 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) carbonyl]-2-naphthylsulfone, described in Example XIV, in 10 cm3 of glacial acetic acid and 0.65 g of powdered zinc is heated at reflux with stirring for 1 hour. There is then slowly added 0.9 cm3 of concentrated HCl. Reflux is again maintained for one hour after the end of the addition of the HCl and there is again added 0.9 cm3HCl. The mixture is then brought for one hour again to the boiling temperature of acetic acid and then left to stand overnight. The next day the reaction mixture is poured into 20 cm3 of 6N HCl and extracted three times with 30 cm3 of ethyl ether. The combined ether phases are washed with water, decanted and dried on sodium sulfate. After evaporation of the solvent 0.5 g of yellow powder is obtained which is then dissolved in methylene chloride. The solution is deposited on a silica gel chromatography column. After concentration of the fractions containing the pure expected product and drying, 0.32 g of ethyl 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) methylene]-2-methylsulfone in the form of white crystals whose melting point is 174° C. is obtained.

Workup

  1. temperatureat reflux
  2. temperatureReflux
  3. temperatureis again maintained for one hour
  4. additionis again added 0.9 cm3HCl
  5. waitleft
  6. waitto stand overnight
  7. extractionextracted three times with 30 cm3 of ethyl ether
  8. washThe combined ether phases are washed with water
  9. customdecanted
  10. customdried on sodium sulfate
  11. customAfter evaporation of the solvent 0.5 g of yellow powder
  12. customis obtained which

Sources & evidence

ORD record
ord-4d9372472cfe470e83832f26e5fdbe63
Source dataset
uspto-grants-1990_12
Patent number
US04980509

Reaction notes

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