Hydrochloric Acid → (1,1-Dimethyl-2-propynyl) 2-chloropropionate

HRID 2116673Notes

Reaction equation

HRID 2116673 reaction equation
[CH3:1][C:2]([CH3:6])([OH:5])[C:3]#[CH:4].[Cl:7][CH:8]([CH3:12])[C:9](Cl)=[O:10].Cl>O>[Cl:7][CH:8]([CH3:12])[C:9]([O:5][C:2]([CH3:6])([CH3:1])[C:3]#[CH:4])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 82582-Methyl-3-butyn-2-olHCID 1110192-Chloropropionyl chloride

Product 1

HCID 54354287(1,1-Dimethyl-2-propynyl) 2-chloropropionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

0.84 g of 1,1-dimethyl-2-propynol and solution F were mixed and stirred for 15 minutes at 0° C. To the mixture was added 0.97 ml of 2-chloropropionyl chloride and the solution was stirred for 5 minutes at 0° C., additional 5 hours at room temperature. Then, to the reaction mixture was added 1N hydrochloric acid and water, and extracted with ethyl acetate. The organic layer was washed successively with water and aqueous solution of sodium bicarbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography to give 1.06 g of (1,1-dimethyl-2-propynyl) 2-chloropropionate.

Workup

  1. stirringthe solution was stirred for 5 minutes at 0° C., additional 5 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water and aqueous solution of sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained

Sources & evidence

ORD record
ord-3ca63c30ccb14cc99644517731c6ce13
Source dataset
uspto-grants-2008_10
Patent number
US07439266B2

Reaction notes

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