Lithium Hydroxide → 3-Methyl-4-(4-methyl-1,3-thiazol-2-yl)benzoic acid

HRID 531256Notes

Reaction equation

HRID 531256 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[S:13][CH:14]=[C:15]([CH3:17])[N:16]=1)[C:5]([O:7]C)=[O:6].[OH-].[Li+]>O1CCOCC1.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[S:13][CH:14]=[C:15]([CH3:17])[N:16]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 90009102Methyl 3-methyl-4-(4-methylthiazol-2-yl)benzoate

Product 1

HCID 900091523-Methyl-4-(4-methyl-1,3-thiazol-2-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 3-methyl-4-(4-methylthiazol-2-yl)benzoate (Step A, 6.0 g, 22.96 mmol) in 1,4-dioxane (5 mL) was added lithium hydroxide (1.65 g, 68.9 mmol) in water (5 mL). Once the reaction was deemed complete by LCMS, it was concentrated in vacuo. The residual white solid was washed with a mixture of dichloromethane/methanol (1/1), and filtered. The filtrate was concentrated to give the title compound as a white solid which was used in the next step without further purification. LCMS (M+H)+: 234.1

Workup

  1. concentrationwas concentrated in vacuo
  2. washThe residual white solid was washed with a mixture of dichloromethane/methanol (1/1)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ea92c2522fd24172863d05b398da1fb3
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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