Hydrochloric Acid → 4-But-2-ynyloxy-benzoic acid

HRID 517487Notes

Reaction equation

HRID 517487 reaction equation
[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6].Cl>O1CCCC1.O.C(OCC)(=O)C>[CH2:3]([O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59324007Methyl 4-but-2-ynyloxybenzoate

Product 1

HCID 222825564-But-2-ynyloxy-benzoic acidYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

26 ml (262 mmol) of an aqueous solution of sodium hydroxide having a concentration of 10N are added to a solution of 13.4 g (65.7 mmol) of methyl 4-but-2-ynyloxybenzoate diluted in 200 ml of tetrahydrofuran and 25 ml of water. The reaction medium is stirred at reflux for 5 h then at 45° C. for 18 h. The reaction medium is hydrolysed, diluted with ethyl acetate then brought to pH=6 using an aqueous solution of hydrochloric acid having a concentration of 1N. The product is extracted with ethyl acetate. The organic phase is washed with water then with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated. 12.5 g (100%) of 4-but-2-ynyloxybenzoic acid are obtained in the form of a white solid.

Workup

  1. temperatureat reflux for 5 h
  2. extractionThe product is extracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-954b80350bad4ace88ebeb1c121c44f2
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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