Sodium Bicarbonate → HCID 13958743, compound

HRID 1834697Notes

Reaction equation

HRID 1834697 reaction equation
[Cl:1][C:2]1[C:15]([Cl:16])=[C:14]([C:17](=[O:22])[C:18](=[CH2:21])[CH2:19][CH3:20])[CH:13]=[CH:12][C:3]=1[O:4][CH:5]([CH3:11])[C:6]([O:8]CC)=[O:7].C(=O)(O)[O-].[Na+]>C(O)C.O>[Cl:1][C:2]1[C:15]([Cl:16])=[C:14]([C:17](=[O:22])[C:18](=[CH2:21])[CH2:19][CH3:20])[CH:13]=[CH:12][C:3]=1[O:4][CH:5]([CH3:11])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 20373925HCID 20373925, compound

Product 1

HCID 13958743HCID 13958743, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2,3-dichloro-4-(2-methylenebutyryl)-phenol (4.90 g., 0.02 mole) in dimethylformamide (20 ml.) is added potassium carbonate (6.08 g., 0.044 mole) and ethyl 2-bromopropionate (7.97 g., 0.044 mole). The reaction mixture is heated at 55°-60° C. for one hour with stirring. The reaction mixture is cooled. Water (50 ml.) is added and the resulting oil is extracted with ether (3 × 100 ml.). The combined ether extracts are dried over anhydrous magnesium sulfate, filtered and the ether is evaporated under reduced pressure to afford ethyl 2-[2,3-dichloro-4-(2-methylenebutyryl)phenoxy]propionate. The ester is dissolved in ethanol (75 ml.) and treated with a solution of sodium bicarbonate (5.04 g., 0.06 mole) in water (150 ml.). The mixture is heated on a steam bath with stirring for 5 hours and then concentrated under reduced pressure to a volume of 50 ml. Water (50 ml.) is added and the solution is acidified to a pH of 4 with hydrochloric acid (6N). The resulting oil is extracted with ether (3 × 100 ml.) and the combined extracts are dried over anhydrous magnesium sulfate. The ether is evaporated under reduced pressure to afford 6.34 g. (100%) of a white, waxy solid. Recrystallization from cyclohexane affords 5 g. (79%) of crude product, m.p. 115°-119° C. Further purification by recrystallization from butyl chloride affords substantially pure 2-[2,3-dichloro-4-(2-methylenebutyryl)phenoxy]propionic acid, m.p., 122.5°-123.5° C.

Workup

  1. temperatureThe mixture is heated on a steam bath
  2. concentrationconcentrated under reduced pressure to a volume of 50 ml
  3. additionWater (50 ml.) is added
  4. extractionThe resulting oil is extracted with ether (3 × 100 ml.)
  5. dry with materialthe combined extracts are dried over anhydrous magnesium sulfate
  6. customThe ether is evaporated under reduced pressure
  7. customto afford 6.34 g
  8. customRecrystallization from cyclohexane
  9. customaffords 5 g
  10. customFurther purification
  11. customby recrystallization from butyl chloride

Sources & evidence

ORD record
ord-4c5cd86fc40141f68d0d01f5d92527e5
Source dataset
uspto-grants-1978_01
Patent number
US04070539

Reaction notes

Loading…