Sulfuric Acid → HCID 15045078, compound

HRID 1089860Notes

Reaction equation

HRID 1089860 reaction equation
[CH3:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]([CH2:15][CH2:16][CH:17]3[O:21]CC[O:18]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.CCOC(C)=O>CC(C)=O.O.CCCCCC>[CH3:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]([CH2:15][CH2:16][C:17]([OH:21])=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 15045077HCID 15045077, compound

Product 1

HCID 15045078HCID 15045078, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A solution of 2-[(4-methylfluoren-9-yl)ethyl]-1,3-dioxolane (11.1 g, 39.6 mmol) in acetone (150 mL) at 0° C. was charged with Jone's reagent (16 g of CrO3 and I6 ml of H2SO4 (conc.) in 100 ml of water). The reaction mixture was stirred overnight at room temperature. The reaction was monitored by TLC (silica, 25% EtOAc in hexane). The acetone was evaporated, the residue was diluted with water (100 mL). The product was extracted into EtOAc and the organic layer was washed thoroughly with water (×6), until aqueous washings were clear, then the product was extracted into 1N NaOH solution (3×70 mL), the water was washed again with ethyl acetate (1×30 mL) and acidified to pH=1. The solid formed was filtered off, washed with water and dried. This afforded 6.8 g (68.2%) of the 3-(4-methylfluoren-9-yl)propionic acid.

Workup

  1. customThe acetone was evaporated
  2. additionthe residue was diluted with water (100 mL)
  3. extractionThe product was extracted into EtOAc
  4. washthe organic layer was washed thoroughly with water (×6), until aqueous washings
  5. extractionthe product was extracted into 1N NaOH solution (3×70 mL)
  6. washthe water was washed again with ethyl acetate (1×30 mL)
  7. customThe solid formed
  8. filtrationwas filtered off
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-aa49da1169b740ad8753e77f3935c38e
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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