Hydrochloric Acid → 4-Oxo-4-phenoxybutanoic acid

HRID 41826Notes

Reaction equation

HRID 41826 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:14]1(=[O:20])[O:19][C:17](=[O:18])[CH2:16][CH2:15]1.Cl>O>[O:20]=[C:14]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 7922Succinic anhydrideHCID 10340Sodium Carbonate

Product 1

HCID 2387224-Oxo-4-phenoxybutanoic acidYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Phenol (1.88 g, 20.0 mmol) was dissolved in a solution of sodium carbonate (anhydrous) (1.06 g, 10.0 mmol) in water (20 ml) and cooled to 0° C. Succinic anhydride (2.00 g, 20.0 mmol) was added and the suspension was allowed to stir at 0° C. for 1 h. The reaction mixture was gradually warmed to room temperature and stirred over night. The clear solution was cooled to 0° C. and acidified to pH 0 (addition of 1M aqueous HCl). The reaction mixture was extracted with chloroform (3×25 ml), dried over Na2SO4, filtered and the solvent removed under reduced pressure to obtain a white solid (1.63 g, 8.4 mmol, 42%). The product was used without any further purification.

Workup

  1. temperatureThe reaction mixture was gradually warmed to room temperature
  2. stirringstirred over night
  3. temperatureThe clear solution was cooled to 0° C.
  4. extractionThe reaction mixture was extracted with chloroform (3×25 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-cc79a73ef75246989c2551724f3d37c1
Source dataset
uspto-grants-2013_09
Patent number
US08535655B2

Reaction notes

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