Ethanol → HCID 21480700, compound

HRID 1490226Notes

Reaction equation

HRID 1490226 reaction equation
[CH2:1](O)C.[Cl:4][C:5]1[CH:18]=[CH:17][C:16]2[CH:15]3[CH2:19][C:8]([C:21]([O:23][CH3:24])=[O:22])([C:9]4[C:14]3=[CH:13][CH:12]=[C:11]([OH:20])[CH:10]=4)[C:7]=2[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].CI>C(OCC)C>[Cl:4][C:5]1[CH:18]=[CH:17][C:16]2[CH:15]3[CH2:19][C:8]([C:21]([O:23][CH3:24])=[O:22])([C:9]4[C:14]3=[CH:13][CH:12]=[C:11]([O:20][CH3:1])[CH:10]=4)[C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21480715HCID 21480715, compound

Product 1

HCID 21480700HCID 21480700, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ethanol solution of methyl 2-chloro-7-hydroxy-9,10-dihydro-9,10-methano-9-anthracenecarboxylate (described in example 90a) was added potassium carbonate and methyl iodide. The suspension was heated to reflux, cooled and diluted with diethyl ether, filtered to remove salts, and concentrated to a solid. The title compound was formed in 90% yield. TLC analysis (Rf 0.40, 20% ethyl acetate in hexane). MS (CI, CH4) m/z 315 (M+1,100), 343 (M+29,13), 301 (38), 287 (9), 279 (14), 265 (6), 255 (42)

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove salts
  6. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-24c41ebdaf274f5b8717eb8f89802161
Source dataset
uspto-grants-1997_10
Patent number
US05681840

Reaction notes

Loading…