Sodium Hydroxide → 2,6-Dichloro-α-methylenebenzenepropanoic acid

HRID 1904582Notes

Reaction equation

HRID 1904582 reaction equation
[OH-].[Na+].[I-].[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[CH2:12][CH:13]([C:19]([O:21]C)=[O:20])[CH2:14][N+](C)(C)C>CO>[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[CH2:12][C:13](=[CH2:14])[C:19]([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20037664HCID 20037664, compound

Product 1

HCID 867431352,6-Dichloro-α-methylenebenzenepropanoic acidYield 112.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under an inert atmosphere, 120 ml of 2N sodium hydroxide were added to 53.3 g of the product of Step B in suspension in 500 ml of methanol. After refluxing the mixture for 2 hours, the solvents were eliminated under reduced pressure, and the residual aqueous phase was extracted with ether. After acidifying with 5N hydrochloric acid, extraction was done again with ether and then with ethyl acetate. The combined organic phases were dried, and the solvents were eliminated under reduced pressure to obtain 32 g of crude product which was crystallized from hexane and then melted at 132° C.

Workup

  1. temperatureAfter refluxing the mixture for 2 hours
  2. extractionthe residual aqueous phase was extracted with ether
  3. extractionAfter acidifying with 5N hydrochloric acid, extraction
  4. customThe combined organic phases were dried

Sources & evidence

ORD record
ord-8603bd97639043758527e18c93b0f839
Source dataset
uspto-grants-1989_06
Patent number
US04839358

Reaction notes

Loading…