Sodium Hydroxide → HCID 58531532, compound

HRID 1889717Notes

Reaction equation

HRID 1889717 reaction equation
[CH2:1]([S:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16]C)=[O:15])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C1COCC1.CO>[CH2:1]([S:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([OH:16])=[O:15])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58531600HCID 58531600, compound

Product 1

HCID 58531532HCID 58531532, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(phenethylthiomethyl)benzoate (1.15 g, 4.02 mmol) in THF (4 mL) and MeOH (4.00 mL) was added 1 N aqueous NaOH solution (6 mL). The resulting mixture was stirred at rt for overnight. The reaction mixture was concentrated in vacuo and the residue was diluted with 1 N HCl solution. The solid was filtered and vacuum dried to give the desired product (1.05 g, 95%) as a white solid. 1H NMR (DMSO-d6) δ 13.07 (s, 1H), 7.93 (s, 1H), 7.83-7.81 (m, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.45 (t, J=8.0 Hz, 1H), 7.29-7.25 (m, 2H), 7.20-7.17 (m, 3H), 3.84 (s, 2H), 2.91-2.78 (m, 2H), 2.63-2.59 (m, 2H). MS (ESI): 273.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with 1 N HCl solution
  3. filtrationThe solid was filtered
  4. customvacuum dried

Sources & evidence

ORD record
ord-4dea14e04777454d93e113f518c44767
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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