Methanol → HCID 54276860, compound

HRID 972267Notes

Reaction equation

HRID 972267 reaction equation
O[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([CH:15]([CH3:19])[C:16](O)=[O:17])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.[N+](=C)=[N-].[C:23](=O)([O-])[O-:24].[K+].[K+].CI.[CH3:31][OH:32]>CC(C)=O>[CH3:31][O:32][C:16](=[O:17])[CH:15]([CH3:19])[C:9]1[CH:8]=[CH:7][C:12]2[C:13]3[C:5](=[CH:4][C:3]([O:24][CH3:23])=[CH:2][CH:14]=3)[CH2:6][C:11]=2[CH:10]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 6328Methyl iodideHCID 9550DiazomethaneHCID 11430Potassium CarbonateHCID 21406499HCID 21406499, compound

Product 1

HCID 54276860HCID 54276860, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 7-hydroxy-α-methylfluorene-2-acetic acid (10.8 g) in methanol is treated with an excess of ethereal diazomethane to prepare the methyl ester. The ester is dissolved in acetone (550 ml) containing potassium carbonate (110 g) treated with methyl iodide (83 ml) and refluxed overnight. The mixture is filtered and the filtrate evaporated to dryness. The residue is treated with ethyl acetate and filtered to give the crude product. A portion of this material is plate chromatographed on silica gel employing chloroform-hexane (1:1) as the developing solvent. Elution of the least polar band with ethyl acetate, evaporation and crystallization of the residue from acetone-isopropyl ether gave the title product (mp 98.5°-100.5°). The analytical sample is prepared by recrystallization from acetone-isopropyl ether, mp 101°-103°.

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe mixture is filtered
  3. customthe filtrate evaporated to dryness
  4. additionThe residue is treated with ethyl acetate
  5. filtrationfiltered
  6. customto give the crude product
  7. customchromatographed on silica gel
  8. washElution of the least polar band
  9. customwith ethyl acetate, evaporation and crystallization of the residue from acetone-isopropyl ether

Sources & evidence

ORD record
ord-b52ab17b2dea448b8a4463cb7405f7c4
Source dataset
uspto-grants-1977_10
Patent number
US04052436

Reaction notes

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