Hydrochloric Acid → 3-(2,3-Dichlorophenoxy)propanoic acid

HRID 871053Notes

Reaction equation

HRID 871053 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:11].[C:12]1(=[O:16])[O:15][CH2:14][CH2:13]1.Cl>O>[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH2:14][CH2:13][C:12]([OH:16])=[O:15]

Participants

6

Procedure

0.4 g (0.01 mol) of Sodium hydroxide was dissolved in 4 ml of water. To this stirred solution was added 1.63 g (0.01 mol) of 2,3-dichloro phenol was added. Once the solid had dissolved the alkaline solution was kept stirring at 100 C for 1 hour. After that β-propiolactone 0.72 g (0.628 ml, 0.01 mol) was added slowly in drops for 5 minutes. The reaction mixture was further continued heating for 12 h. The reaction mixture was cooled to room temperature and water 10 ml was added. This diluted mixture was acidified by the addition of Con. HCl. The product was extracted twice with diethyl ether (20 ml). The ether layer was then washed with 10% Sodium bicarbonate. The aqueous layer was acidified to pH=2. The precipitated solid was filtered and dried to afford the required product 3-(2,3-dichlorophenoxy)propanoic acid.

Workup

  1. additionwas added
  2. dissolutionOnce the solid had dissolved the alkaline solution
  3. temperatureThe reaction mixture was further continued heating for 12 h
  4. additionThis diluted mixture was acidified by the addition of Con
  5. extractionThe product was extracted twice with diethyl ether (20 ml)
  6. washThe ether layer was then washed with 10% Sodium bicarbonate
  7. filtrationThe precipitated solid was filtered
  8. customdried

Sources & evidence

ORD record
ord-082e58e1c13b4e0386977e2bbf3129dd
Source dataset
uspto-grants-2015_03
Patent number
US08969573B2

Reaction notes

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