Methyl iodide → HCID 70633583, compound

HRID 1729900Notes

Reaction equation

HRID 1729900 reaction equation
[CH3:1][C:2]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([OH:19])=[O:18].[C:20](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:1][C:2]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:20])[CH:11]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 70633216HCID 70633216, compound

Product 1

HCID 70633583HCID 70633583, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 59mg. of methyl 7-hydroxyfluorene-2-acetic acid, 1.3g. of potassium carbonate, and 0.5ml. methyl iodide in 11ml. of acetone is refluxed for 22 hr., filtered and the solid washed with additional acetone. The filtrate is evaporated and the residue plate chromatographed on silica gel employing chloroform-hexane (2:1) as the developing solvent. Elution of the least polar band with ethyl acetate, evaporation and crystallization of the residue from ethyl acetate-isopropyl ether gives 17mg. of the title compound, mp 114-115°. Recrystallization from ethyl acetate-isopropyl ether gives the analytical sample, mp 114.5°-115.5°; λKBr 5.80μ.

Workup

  1. additionA mixture of 59mg
  2. filtration, filtered
  3. washthe solid washed with additional acetone
  4. customThe filtrate is evaporated
  5. customthe residue plate chromatographed on silica gel
  6. washElution of the least polar band
  7. customwith ethyl acetate, evaporation and crystallization of the residue from ethyl acetate-isopropyl ether
  8. customgives 17mg

Sources & evidence

ORD record
ord-c06bc9357841480f96c0ccb5a89e5f8b
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

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