Phenol → 3-Phenoxypropionic acid

HRID 1439809Notes

Reaction equation

HRID 1439809 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl[CH2:11][CH2:12][C:13]([OH:15])=[O:14]>O>[O:7]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 78993-Chloropropionic acidHCID 14797Potassium Hydroxide2×

Product 1

HCID 815963-Phenoxypropionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Phenol (203 g, 2.16 moles) is added to a solution of potassium hydroxide (112 g, 2.0 mole) in water (100 ml) at 70° C. The resulting solution is maintained at a temperature of 70° C and small portions of 3-chloropropionic acid (101 g, 0.93 mole) in water (100 ml) and potassium hydroxide (44 g, 0.81 mole) in water (50 ml) are added alternately over a period of 0.5 hour. The reaction solution is heated at reflux temperature for 10 min., cooled to room temperature and washed with ether. The aqueous phase is acidified with hydrochloric acid and extracted with ether. The combined ethereal extracts are shaken with sodium carbonate solution. The aqueous part is acidified with hydrochloric acid and extracted with ether. The combined organic extracts are dried, evaporated and crystallized from ether-petroleum ether to give the title compound, m.p. 95°-97° C [lit. m.p. 97°-98° C as reported by S. G. Powell, J. Amer. Chem. Soc., 45, 2711 (1923)].

Workup

  1. additionare added alternately over a period of 0.5 hour
  2. temperatureThe reaction solution is heated
  3. temperatureat reflux temperature for 10 min.
  4. washwashed with ether
  5. extractionextracted with ether
  6. extractionextracted with ether
  7. customThe combined organic extracts are dried
  8. customevaporated
  9. customcrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-1911a5a62be24411bd6ffc7308a4502f
Source dataset
uspto-grants-1977_11
Patent number
US04060619

Reaction notes

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