Ethanol → 55845-76-6

HRID 863583Notes

Reaction equation

HRID 863583 reaction equation
COC1C=CC(C)=CC=1[CH:5]=[S:6].C[CH2:13][OH:14].[OH2:15].[OH2:16].O.O.O.O.[Mg+2].C(O[O-])(=O)[C:23]1[C:24](=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:25]([O-:27])=O>O>[CH3:13][O:14][C:23]1[CH:31]=[CH:30][C:29]([S:6]([CH3:5])(=[O:16])=[O:15])=[CH:28][C:24]=1[CH:25]=[O:27]

Participants

5

Reactant 3

HCID 702EthanolHCID 19696574HCID 19696574, compoundHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)

Product 1

HCID 1893897455845-76-6

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Under N2 in a round-bottomed flask fitted with a condensor, 2-methoxy-5-methylthiobenzaldehyde (0.89 g, 4.9 mmol) was added to 0.6 mL of EtOH. To this, a solution of monoperoxyphthalic acid magnesium salt hexahydrate (2.41 g, 4.9 mmol) in 10.4 mL of H2O was added and the mixture was heated at 95° C. for 18 hours. The reaction was then quenched with 10 mL of H2O, extracted with CH2Cl2 (4×10 mL) and the combined organics were dried over MgSO4 and concentrated in vacuo to an oil, 0.34 g. Flash chromatography on silica gel, eluting with EtOAc:hexanes (2.98) gave the pure title compound as a white solid, 0.36 g, m.p. 140°-143° C. 1H NMR (CDCl3) δ3.05 (s, 3H), 4.05 (s, 3H), 7.2 (d, 1H), 8.15 (dd, 1H), 8.40 (d, 1H), 10.5 (s, 1H).

Workup

  1. customThe reaction was then quenched with 10 mL of H2O
  2. extractionextracted with CH2Cl2 (4×10 mL)
  3. dry with materialthe combined organics were dried over MgSO4
  4. concentrationconcentrated in vacuo to an oil, 0.34 g
  5. washFlash chromatography on silica gel, eluting with EtOAc

Sources & evidence

ORD record
ord-fa46741e95914e31be35632d9c77aa44
Source dataset
uspto-grants-1998_02
Patent number
US05721255

Reaction notes

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