Beta-Propiolactone → HCID 20135581, compound

HRID 579990Notes

Reaction equation

HRID 579990 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:12]1(=[O:16])[O:15][CH2:14][CH2:13]1>[OH-].[Na+].CCOCC>[Cl:10][C:9]1[C:2]([Cl:1])=[C:3]([CH:4]=[O:5])[CH:6]=[CH:7][C:8]=1[O:11][CH2:14][CH2:13][C:12]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 2365Beta-PropiolactoneHCID 5283802,3-Dichloro-4-hydroxybenzaldehyde

Product 1

HCID 20135581HCID 20135581, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

2,3-dichloro-4-hydroxybenzaldehyde (38.2 g., 0.2 mole) is dissolved in a 10% sodium hydroxide solution (200 ml.). The solution is heated to boiling and β-propiolactone (144 g., 2.0 moles) is added dropwise at such a rate as to keep the solution boiling. During the addition 10% sodium hydroxide solution is added in portions to maintain an alkaline mixture. Then the solution is cooled and acidified. The precipitated material is dissolved in ether and the product is extracted into a 5% sodium bicarbonate solution. Acidification of the aqueous solution precipitates 3-(2,3-dichloro-4-formylphenoxy)propionic acid, which is purified by recrystallization from ethyl acetate.

Workup

  1. additionis added dropwise at such a rate as
  2. additionis added in portions
  3. temperatureto maintain an alkaline mixture
  4. temperatureThen the solution is cooled
  5. extractionthe product is extracted into a 5% sodium bicarbonate solution
  6. customAcidification of the aqueous solution precipitates 3-(2,3-dichloro-4-formylphenoxy)propionic acid, which
  7. customis purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-34c4669876e5496c9e800ddd0ff089ff
Source dataset
uspto-grants-1988_06
Patent number
US04751244

Reaction notes

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