Hydrochloric Acid → 4-(4-Cyclopropylbuta-1,3-diyn-1-yl)benzoic acid

HRID 1519679Notes

Reaction equation

HRID 1519679 reaction equation
CO.[OH-].[Na+].C[O:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]#[C:17][CH:18]2[CH2:20][CH2:19]2)=[CH:10][CH:9]=1.Cl>O.C(OCC)(=O)C.O1CCOCC1>[CH:18]1([C:17]#[C:16][C:15]#[C:14][C:11]2[CH:10]=[CH:9][C:8]([C:7]([OH:21])=[O:6])=[CH:13][CH:12]=2)[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 866792584-(4-Cyclopropylbuta-1,3-diyn-1-yl)benzoic acid methyl ester

Product 1

HCID 594169284-(4-Cyclopropylbuta-1,3-diyn-1-yl)benzoic acidYield 96.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Methanol (3.0 mL), 1,4-dioxane (3.0 mL), and a 20% aqueous solution (1.5 mL) of sodium hydroxide were added to 4-(4-cyclopropylbuta-1,3-diyn-1-yl)benzoic acid methyl ester (0.31 g) as obtained in Example 6-(1), whereafter the mixture was stirred for 2.5 hours at room temperature. Ethyl acetate and water were added, and the mixture was adjusted to pH 3 with 6 mol/L of hydrochloric acid to isolate the organic layer. The extract was dried over anhydrous magnesium sulfate, and then the desiccant was filtered out. The solvent was distilled off under reduced pressure to obtain 4-(4-cyclopropylbuta-1,3-diyn-1-yl)benzoic acid (dark brown solid) (0.28 g, 94%).

Workup

  1. customas obtained in Example 6-(1), whereafter the mixture
  2. customto isolate the organic layer
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationthe desiccant was filtered out
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a28bfb475a69443088986405af30e4f0
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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