Ethanol → HCID 21480700, compound

HRID 1721801Notes

Reaction equation

HRID 1721801 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-dfd75da73d1c4be3b88e57986992070e
Source dataset
uspto-grants-1996_04
Patent number
US05512575

Reaction notes

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