Methanol → 3-Hydroxy-5-(trifluoromethyl)thiophene-2-carboxylic acid

HRID 23324Notes

Reaction equation

HRID 23324 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[S:4][C:3]=1[C:11]([O:13]C)=[O:12].CO.[OH-].[Na+]>O>[OH:1][C:2]1[CH:6]=[C:5]([C:7]([F:10])([F:8])[F:9])[S:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 2759855Methyl 3-hydroxy-5-(trifluoromethyl)thiophene-2-carboxylate

Product 1

HCID 27593483-Hydroxy-5-(trifluoromethyl)thiophene-2-carboxylic acidYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5B (2.38 g) and methanol (20 ml) was added to a stirred solution of sodium hydroxide (1.68 g) in water (20 ml). The reaction mixture was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The concentrate was cooled to 5° C. and acidified with concentrated HCl (3.5 ml). The resulting suspension was stirred at 5° C. for 30 minutes. The solid was collected by filtration, washed with water, then dried in vacuo at 35-40° C. to give the free acid (1.45 g, 65%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. temperatureThe concentrate was cooled to 5° C.
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customdried in vacuo at 35-40° C.

Sources & evidence

ORD record
ord-c0e26b6ca5084e8b9c91033f3a1ae772
Source dataset
uspto-grants-2005_02
Patent number
US06852673B2

Reaction notes

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