Hydrochloric Acid → 3-(4-Hydroxyphenyl)hex-4-ynoic acid

HRID 922269

Reaction equation

HRID 922269 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]2C(=O)OC(C)(C)[O:14][C:13]2=[O:21])[C:9]#[C:10][CH3:11])=[CH:4][CH:3]=1.O.Cl>C(C(CC)=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]#[C:10][CH3:11])[CH2:12][C:13]([OH:21])=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 598551335-(1-(4-Hydroxyphenyl)but-2-yn-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 598551363-(4-Hydroxyphenyl)hex-4-ynoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Procedure

To a 250 mL 3-necked RB flask fitted with magnetic stirrer was charged with 5-[1-(4-hydroxyphenyl)but-2-yn-1-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione (5.8 g, 20.13 mmol) in diethyl ketone was added water (13 mL), the reaction mixture was heated to refluxed for 48 h. The RM was acidified with 1N HCl and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulphat. Finally removal of solvent under reduced pressure to obtain the product (4.11 g, yield: 100.0%).

Workup

  1. customTo a 250 mL 3-necked RB flask fitted with magnetic stirrer
  2. temperaturethe reaction mixture was heated
  3. temperatureto refluxed for 48 h
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulphat
  7. customFinally removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-41fff5c63dc54b33b6a24ec418b79b06
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Linked notes

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