Acetic Acid → HCID 54932878, compound

HRID 1908080Notes

Reaction equation

HRID 1908080 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:6]([O:8]CC)=[O:7].OS(O)(=O)=O.CC(O)=O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:18])=[O:19])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 58551316HCID 58551316, compound

Product 1

HCID 54932878HCID 54932878, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 3-methoxy-4-(2-(methylsulfonyl)ethoxy)benzoate (30 mg, 0.099 mmol) was taken up in water (1.2 mL), H2SO4 (200 μL, 3.8 mmol), and AcOH (1300 μL, 23 mmol). The mixture was heated at 90° C. for 6 h before it was cooled to ambient temperature and was concentrated under vacuum. The residue was purified by column chromatography (1-40% MeOH/DCM) to give 3-methoxy-4-(2-(methylsulfonyl)ethoxy)benzoic acid. ESI-MS m/z calc. 274.1. found 275.1 (M+1)+; Retention time: 0.69 minutes (3 min run).

Workup

  1. temperaturewas cooled to ambient temperature
  2. concentrationwas concentrated under vacuum
  3. customThe residue was purified by column chromatography (1-40% MeOH/DCM)

Sources & evidence

ORD record
ord-5d4033af05c240618b82ad28c7b997c5
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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