Hydrochloric Acid → HCID 67401877, compound

HRID 906109Notes

Reaction equation

HRID 906109 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=[O:9].[OH-].[K+].Cl>CO.O>[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 67402660HCID 67402660, compound

Product 1

HCID 67401877HCID 67401877, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2-(4-hydroxybut-1-yn-1-yl)-3-(methyloxy)benzoate (0.056 g, 0.24 mmol) was dissolved in methanol (2 ml), and a solution of potassium hydroxide (0.027 g, 0.48 mmol) in water (0.5 ml) was added. The reaction mixture was stirred at 60° C. for 1 h, cooled to room temperature, and 1.5M hydrochloric acid was added to pH 4. The aqueous mixture was extracted with ethyl acetate, and the organic layer was washed with brine then dried over sodium sulfate. The mixture was then filtered and concentrated to give 2-(4-hydroxybut-1-yn-1-yl)-3-(methyloxy)benzoic acid (0.052 g, 99% yield). MS (EI) for C12H12O4: 219 (M−H).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe aqueous mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationThe mixture was then filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-63d9d8e13718418fadf74cf281a8491b
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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