Hydrochloric Acid → 2-Ethoxybenzoic acid

HRID 2055897

Reaction equation

HRID 2055897 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([O:8]CC)=[O:7])[CH3:2].CC(C)([O-])C.[K+].CCCCCC.C(OCC)(=O)C.Cl>CS(C)=O>[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 221644Benzoic acid, 2-ethoxy-, ethyl esterHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 672522-Ethoxybenzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of Ethyl 2-Ethoxy-benzoate (10 g, 240 mmol) in dimethyl sulfoxide (40 mL) was added potassium tert-butoxide (10 g, 890 mmol) in portions. The solution was heated to 70° C. on a water bath for 2 h, and the progress of the reaction was monitored by TLC using a hexane-ethyl acetate (8:2) solvent system. The reaction mass was cooled to 10° C., poured into ice water, and then acidified with 5% dilute hydrochloric acid. The precipitated solid was filtered and washed thoroughly with distilled water, and the crude mass was recrystallized in hexane (50 mL) to yield an off-white solid of 2-Ethoxy-benzoic Acid (7.6 g, 80%).

Workup

  1. temperatureThe reaction mass was cooled to 10° C.
  2. filtrationThe precipitated solid was filtered
  3. washwashed thoroughly with distilled water
  4. customthe crude mass was recrystallized in hexane (50 mL)

Sources & evidence

ORD record
ord-d6474041cef74729ae621b5df86ffffc
Source dataset
uspto-grants-2008_02
Patent number
US07332629B2

Linked notes

Loading…