Ethanol → HCID 13832246, compound

HRID 2291630Notes

Reaction equation

HRID 2291630 reaction equation
[OH:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S(=O)(=O)(O)O.[CH2:24](O)[CH3:25]>>[OH:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([CH2:8][CH2:9][C:10]([O:12][CH2:24][CH3:25])=[O:11])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1283563-(4-Hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)propanoic acid

Product 1

HCID 13832246HCID 13832246, compound

Procedure

To a solution of 3-(4-hydroxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionic acid (80 g) in ethanol (3.2 () was added dropwise conc. sulfuric acid (160 ml) over a period of 0.5 hour and the mixture was stirred for 2.5 hours at ambient temperature. Evaporation of ethanol gave a residue which was poured into ice-cold water (2.4 () and extracted with chloroform. The extract was washed with water and brine successively and evaporated to dryness to give ethyl 3-(4-hydroxy-5-oxo-3-phenyl2,5-dihydro-2-furyl)propionate which was recrystallized from diisopropyl ether (87.05 g).

Workup

  1. customEvaporation of ethanol
  2. customgave a residue which
  3. additionwas poured into ice-cold water (2.4 ()
  4. extractionextracted with chloroform
  5. washThe extract was washed with water and brine successively
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f5cee193dbe449099220dc76f6392f73
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

Loading…