Tetrahydrofuran → 3-(4,5,6,7-Tetrahydrobenzothiazol-2-ylmethoxy)benzoic acid

HRID 1602492Notes

Reaction equation

HRID 1602492 reaction equation
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17]C)=[O:16].O1CCCC1.[OH-].[Na+]>CO>[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 19611521Methyl 3-(4,5,6,7-tetrahydrobenzothiazol-2-ylmethoxy)benzoate

Product 1

HCID 196115783-(4,5,6,7-Tetrahydrobenzothiazol-2-ylmethoxy)benzoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-(4,5,6,7-tetrahydrobenzothiazol-2-ylmethoxy)benzoate (361 mg, 1.2 mmol), tetrahydrofuran (2 ml), methanol (2 ml) and 1 N sodium hydroxide (2 ml) was stirred at room temperature for 12 hours and then concentrated under reduced pressure. The resulting residue was dissolved in water and the solution was adjusted to pH 3 by adding 10% citric acid aqueous solution. Thereafter, the solid substance formed was collected by filtration, washed with water, and then dried under reduced pressure to give 3-(4,5,6,7-tetrahydrobenzothiazol-2-ylmethoxy)benzoic acid (257 mg, 0.89 mmol, 75%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in water
  3. additionby adding 10% citric acid aqueous solution
  4. customThereafter, the solid substance formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-a7e677c24d794a738ca9e02d5e8b4ac4
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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