Hydrochloric Acid → HCID 54463355, compound

HRID 726854Notes

Reaction equation

HRID 726854 reaction equation
Cl[CH:2]([F:4])[F:3].[CH3:5][O:6][C:7](=[O:26])[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25])=[CH:9][OH:10].C1OCCOCCOCCOCCOC1.[OH-].[Na+].Cl>CN1CCCC1=O.O>[CH3:5][O:6][C:7](=[O:26])[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25])=[CH:9][O:10][CH:2]([F:4])[F:3]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 3633615-Crown-5HCID 67650646HCID 67650646, compound

Product 1

HCID 54463355HCID 54463355, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
5 °C

Procedure

With vigorous stirring at 5° C., chlorodifluoromethane is passed into a solution of 5.7 g of 3-hydroxy-2-[2-(2-methylphenoxymethyl)phenyl]-acrylic acid methyl ester and 0.19 g of 15-crown-5 in 95 ml of N-methylpyrrolidone while simultaneously adding dropwise a solution of 5.34 g of sodium hydroxide in 6.7 ml of water and the reaction mixture is left to react for 1.5 hours. The reaction mixture is then poured onto ice-water, acidified with 4N hydrochloric acid and extracted exhaustively with ethyl acetate. The combined organic phases are washed with a sodium chloride solution, dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography on silica gel with hexane/ethyl acetate (9:1) yields pure 3-difluoromethoxy-2-[2-(2-methylphenoxymethyl)phenyl]-acrylic acid methyl ester in the form of a highly viscous oil that crystallises upon being left to stand. M.p.: sinlets from 68° C., clear molten at 77° C. MS: role 348 M+ (6), 241 (100)

Workup

  1. waitthe reaction mixture is left
  2. customto react for 1.5 hours
  3. additionThe reaction mixture is then poured onto ice-water
  4. extractionextracted exhaustively with ethyl acetate
  5. washThe combined organic phases are washed with a sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-de0b9e876a2b40f099ce74ead459be32
Source dataset
uspto-grants-1998_01
Patent number
US05710314

Reaction notes

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