HCID 15045041, compound → 3-(9H-Fluoren-9-yl)propanoic acid

HRID 2259275Notes

Reaction equation

HRID 2259275 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][CH2:15][CH:16]3[O:20]CC[O:17]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>[CH:1]1[C:13]2[CH:12]([CH2:14][CH2:15][C:16]([OH:20])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 15045041HCID 15045041, compound

Product 1

HCID 135008763-(9H-Fluoren-9-yl)propanoic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 131709961Jones' reagentSolvent

Procedure

3-(9-Fluorenyl)propionic acid was prepared from 2-(9-fluorenyl)ethyl-1,3-dioxolane (50.0 g, 187 mmol) which was dissolved in 20 ml of acetone and 450 ml of Jones' reagent (64 g chromic acid and 64 ml of sulfuric acid in 400 ml of water). After the reaction was complete, the acetone was evaporated, the residue taken into ethyl acetate, washed with water, and organic layer extracted with 1N sodium hydroxide which was acidified with 10% HCl to yield a tan precipitate. FTIR 1954, 1913, 1707, 1429, 1316, 1257, 1208, 948, 933, 735 cm-1. 1H NMR (300 MHz, DMSO-dis) δ 1.84 (t, 2H, J=7.5 Hz), 2.21 (m, 2H), 4.03 (t, 2H, J=5.5 Hz), 7.28-7.38 (m, 4H), 7.56 (d, 2H, J=7.0 Hz), 7.84 (d, 2H, J=7.0 Hz).

Workup

  1. customthe acetone was evaporated
  2. washwashed with water, and organic layer
  3. extractionextracted with 1N sodium hydroxide which
  4. customto yield a tan precipitate

Sources & evidence

ORD record
ord-84ef42d6a0ff4e66bd7725248f6d1b14
Source dataset
uspto-grants-1995_12
Patent number
US05472973

Reaction notes

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