4-Chlororesorcinol → HCID 67166662, compound

HRID 1626404Notes

Reaction equation

HRID 1626404 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[OH:9].[Cl:10][CH2:11][CH2:12][C:13](O)=[O:14].C(OCC)(=O)C>FC(F)(F)S(O)(=O)=O>[Cl:10][CH2:11][CH2:12][C:13]([C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([OH:9])=[CH:4][C:5]=1[OH:8])=[O:14]

Participants

5

Reactant 3

HCID 17314-ChlororesorcinolHCID 78993-Chloropropionic acidHCID 8857Ethyl Acetate

Product 1

HCID 67166662HCID 67166662, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

A solution of 4-chlorobenzene-1,3-diol (100 g, 692 mmol) and 3-chloropropanoic acid (75.1 g, 692 mmol) in trifluoromethanesulfonic acid (295 mL) was stirred at 75° C. for 30 minutes. The reaction was cooled to ambient temperature and slowly poured into a 2 L beaker filled with ice. To the slurry was added ethyl acetate (1200 mL) with stirring until all solids dissolved. The mixture was poured into a reparatory funnel, the aqueous layer was removed and the organic layer was washed with water. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel column chromatography eluting with a solvent system mixture of 15% ethyl acetate/hexanes to provide the desired product (162.6 g, 86%).

Workup

  1. additionslowly poured into a 2 L
  2. additionbeaker filled with ice
  3. dissolutiondissolved
  4. additionThe mixture was poured into a reparatory funnel
  5. customthe aqueous layer was removed
  6. washthe organic layer was washed with water
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was purified by silica gel column chromatography
  11. washeluting with a solvent system mixture of 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6f04d1990c2b417eb517c136a4eb23df
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

Loading…