Water → HCID 20373925, compound

HRID 1834696Notes

Reaction equation

HRID 1834696 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:14])[C:10](=[CH2:13])[CH2:11][CH3:12])[CH:5]=[CH:4][C:3]=1[OH:15].C(=O)([O-])[O-].[K+].[K+].Br[CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CN(C)C=O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:14])[C:10](=[CH2:13])[CH2:11][CH3:12])[CH:5]=[CH:4][C:3]=1[O:15][CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 23035905HCID 23035905, compound

Product 1

HCID 20373925HCID 20373925, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 reaction mixture is heated at 55°-60° C. for one hour
  2. temperatureThe reaction mixture is cooled
  3. extractionthe resulting oil is extracted with ether (3 × 100 ml.)
  4. dry with materialThe combined ether extracts are dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe ether is evaporated under reduced pressure

Sources & evidence

ORD record
ord-d4689cb7ba034622b133bb3e505dc6ea
Source dataset
uspto-grants-1978_01
Patent number
US04070539

Reaction notes

Loading…