4-Chlororesorcinol → HCID 67166662, compound

HRID 1021333Notes

Reaction equation

HRID 1021333 reaction equation
FC(F)(F)S(O)(=O)=O.[Cl:9][C:10]1[CH:16]=[CH:15][C:13]([OH:14])=[CH:12][C:11]=1[OH:17].[Cl:18][CH2:19][CH2:20][C:21](O)=[O:22]>O>[Cl:18][CH2:19][CH2:20][C:21]([C:15]1[CH:16]=[C:10]([Cl:9])[C:11]([OH:17])=[CH:12][C:13]=1[OH:14])=[O:22]

Participants

5

Reactant 3

HCID 17314-ChlororesorcinolHCID 78993-Chloropropionic acidHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 67166662HCID 67166662, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
6 °C

Procedure

A 2-liter 4-neck round-bottom flask was charged with trifluoromethanesulfonic acid (500 g, 3.33 mol) and the flask contents were cooled below 10° C. 4-Chlororesorcinol (100 g, 0.69 mol) was added in portions over 20-30 minutes, maintaining the temperature at 4 to 8° C. The reaction mixture was stirred at or below 10° C. until a clear solution formed (40 minutes). 3-Chloropropanoic acid (78.8 g, 0.73 mol) was warmed until melted and then added in liquid form dropwise over 45 minutes to the flask, maintaining the temperature at or below 10° C. The reaction mixture was stirred for an additional 10 minutes at or below 10° C., then slowly heated to 50-55° C. and maintained there for 6 hours. The reaction mixture was cooled to ambient temperature and added dropwise to water (1.1 L) contained in a 3-liter 4-neck round-bottom flask. The resulting mixture was stirred at ambient temperature for 30 minutes. The resulting precipitate was collected by filtration, washed with water (3×540 mL), and dried in a fan dryer at 40° C. until the moisture content fell below 0.5%, to afford 3-chloro-1-(5-chloro-2,4-dihydroxyphenyl)propan-1-one as an orange solid (160 g, 98.4% yield).

Workup

  1. temperaturethe flask contents were cooled below 10° C
  2. customformed (40 minutes)
  3. additionadded in liquid form dropwise over 45 minutes to the flask
  4. temperaturemaintaining the temperature at or below 10° C
  5. stirringThe reaction mixture was stirred for an additional 10 minutes at or below 10° C.
  6. temperatureslowly heated to 50-55° C.
  7. temperaturemaintained there for 6 hours
  8. temperatureThe reaction mixture was cooled to ambient temperature
  9. customcontained in a 3-liter 4-neck round-bottom flask
  10. stirringThe resulting mixture was stirred at ambient temperature for 30 minutes
  11. filtrationThe resulting precipitate was collected by filtration
  12. washwashed with water (3×540 mL)
  13. customdried in a fan dryer at 40° C. until the moisture content

Sources & evidence

ORD record
ord-cb65112768fe4931a99f6c2086b8985a
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

Loading…