Hydrochloric Acid → 6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic Acid

HRID 722279Notes

Reaction equation

HRID 722279 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17]CC)=[O:16])=[CH:7][C:6]=2[CH:20]=1.[OH-].[Li+].Cl>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([F:13])([F:12])[F:14])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 15458898ethyl 6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 97956526-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic AcidYield 85.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of the ester from Step 1 (13.02 g, 42 mmole) was dissolved in 200 mL of methanol and 20 mL of water, treated with lithium hydroxide (5.36 g, 0.128 mole) and stirred at room temperature for 16 hours. The reaction mixture was acidified with 1.2 N HCl, whereupon a solid formed that was isolated by filtration. The solid was washed with 200 mL of water and 200 mL of hexanes and dried in vacuo to afford the title compound as a yellow solid (10.00 g, 85%): mp 181–184° C.

Workup

  1. customformed that
  2. customwas isolated by filtration
  3. washThe solid was washed with 200 mL of water and 200 mL of hexanes
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dfbb327686854db689e88372095bcb9d
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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