3-Chloropropionic acid → HCID 21440943, compound

HRID 329041Notes

Reaction equation

HRID 329041 reaction equation
[Na].[CH2:2]([OH:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[CH2:11][CH2:12][C:13]([OH:15])=[O:14]>O>[CH2:2]([O:9][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 78993-Chloropropionic acidHCID 8129HeptanolHCID 5360545Sodium

Product 1

HCID 21440943HCID 21440943, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

25.3 g (1.1 mole) of sodium dissolved in 464.8 g (4 mole) of heptyl alcohol was heated to 150° C and 54 g (0.49 mole) of 3-chloropropionic acid were added thereto dropwise with stirring. The mixture was heated for a further 2 hours and a precipitate appeared. The mixture was cooled and 1.5 liters of water were added. The mixture was extracted with ether and the aqueous phase was acidified with concentrated sulfuric acid. The mixture was extracted with ether and the ether phase was washed with water, dried and was concentrated. The residue was rectified to obtain 49 g (52% yield) of 3-heptyloxy-propionic acid as a colorless oil boiling at 165° C at 15 mm Hg and having a refractive index nD22 = 1.436.

Workup

  1. temperatureThe mixture was heated for a further 2 hours
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was extracted with ether
  4. extractionThe mixture was extracted with ether
  5. washthe ether phase was washed with water
  6. customdried
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-dd4a9e239a704a1395aceaa65df1903d
Source dataset
uspto-grants-1977_04
Patent number
US04018922

Reaction notes

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