HCID 15045094, compound → 3-(1-Methylfluoren-9-yl)propionic acid

HRID 1089853Notes

Reaction equation

HRID 1089853 reaction equation
[CH3:1][C:2]1[C:14]2[CH:13]([CH2:15][CH2:16][CH:17]3[O:21]CC[O:18]3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.CCCCCC>CC(C)=O>[CH3:1][C:2]1[C:14]2[CH:13]([CH2:15][CH2:16][C:17]([OH:21])=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15045094HCID 15045094, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 150450953-(1-Methylfluoren-9-yl)propionic acidYield 59.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-[2-(1-Methylfluoren-9-yl)ethyl]-1,3-dioxolane (4.8 g, 17.2 mmol) in 100 mL of acetone was charged slowly with John's reagent (CrO3 : H2SO4 :H2O 4:4:50 by weight) at room temperature. The reaction was monitored by TLC (silica, 10% ethyl acetate/hexane). The reaction mixture was stirred for 6 hr at room temperature, the acetone was evaporated and the residual water was extracted with ethyl acetate twice. The combined organic layers were washed with water until water became colorless. The organic solution was then extracted with 1N aqueous solution of sodium hydroxide. The basic aqueous solution was washed with ethyl acetate, acidified and extracted with ethyl acetate again. The ethyl acetate solution was dried over magnesium sulfate and evaporated. Purification of the crude by short path chromatography (silica, 25% ethyl acetate/hexane) afforded 2.6 g (59.9%) of 3-(1-methylfluoren-9-yl)propionic acid.

Workup

  1. customthe acetone was evaporated
  2. extractionthe residual water was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with water until water
  4. extractionThe organic solution was then extracted with 1N aqueous solution of sodium hydroxide
  5. washThe basic aqueous solution was washed with ethyl acetate
  6. extractionextracted with ethyl acetate again
  7. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  8. customevaporated
  9. customPurification of the crude by short path chromatography (silica, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-832c37d086984e9abaf0bb7f753c91cd
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

Loading…