Hydrochloric Acid → HCID 66973846, compound

HRID 1474067Notes

Reaction equation

HRID 1474067 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:5]=[C:6]([CH:10]([C:16]([O:18]CC)=[O:17])[C:11]([O:13]CC)=[O:12])[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+].Cl.[Cl-].[Na+]>>[F:1][C:2]([F:21])([F:22])[O:3][C:4]1[CH:5]=[C:6]([CH:10]([C:16]([OH:18])=[O:17])[C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 66973795HCID 66973795, compound

Product 1

HCID 66973846HCID 66973846, compoundYield 90.4%

Procedure

Diethyl 3-trifluoromethoxyphenylmalonate (3.00 g, 9.38 mmol) was stirred in an aqueous sodium hydroxide solution (15 g, 20% by weight) at 65° C. for 10 min. The reaction mixture was then cooled in an ice bath, and ice (7 g) was added to the reaction mixture, followed by 6 N hydrochloric acid to adjust the pH to about 2. The aqueous mixture was saturated with sodium chloride and extracted with ethyl acetate three times. The combined organic phases were dried (MgSO4) and concentrated to give a solid, which was triturated with a mixture of 33% diethyl ether/hexane to give the title compound as a white solid (2.24 g).

Workup

  1. temperatureThe reaction mixture was then cooled in an ice bath
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. concentrationconcentrated
  5. customto give a solid, which
  6. customwas triturated with a mixture of 33% diethyl ether/hexane

Sources & evidence

ORD record
ord-85f62159b74942348c6810a3e96d1037
Source dataset
uspto-grants-2015_04
Patent number
US09018220B2

Reaction notes

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