Hydrochloric Acid → HCID 59202346, compound

HRID 1673184Notes

Reaction equation

HRID 1673184 reaction equation
C1COCC1.C([O:9][C:10](=[O:24])[C:11]1[CH:16]=[C:15]([F:17])[C:14]([O:18][CH2:19][C:20]#[CH:21])=[C:13]([F:22])[C:12]=1[F:23])C#C.O.[OH-].[Li+].Cl>O>[CH2:19]([O:18][C:14]1[C:15]([F:17])=[CH:16][C:11]([C:10]([OH:24])=[O:9])=[C:12]([F:23])[C:13]=1[F:22])[C:20]#[CH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59202347HCID 59202347, compound

Product 1

HCID 59202346HCID 59202346, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of 10 ml of THF and 10 ml of water, 6.5 g of the obtained 4-(2-propynyloxy)-2,3,5-trifluorobenzoic acid 2-propynyl ester and 2.0 g of lithium hydroxide monohydrate were added, followed by stirring at room temperature for 2 hours and further stirring at 50° C. for 2 hours. The reaction mixture obtained by concentration under reduced pressure until the entire volume was reduced to about half was acidified by adding hydrochloric acid and the obtained solid was collected by filtration. The solid was dried and washed with hexane, and 4.0 g of 4-(2-propynyloxy)-2,3,5-trifluorobenzoic acid was obtained.

Workup

  1. stirringfurther stirring at 50° C. for 2 hours
  2. customThe reaction mixture obtained by concentration under reduced pressure until the entire volume
  3. filtrationthe obtained solid was collected by filtration
  4. customThe solid was dried
  5. washwashed with hexane

Sources & evidence

ORD record
ord-ce9a8ed288f74570a833f820648f3186
Source dataset
uspto-grants-2011_08
Patent number
US07999136B2

Reaction notes

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