Ethanol → HCID 21638546, compound

HRID 1391783Notes

Reaction equation

HRID 1391783 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[C:4]([O:13][CH3:14])[CH:3]=1.OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[CH3:26][CH2:27]O>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:26][CH3:27])=[O:11])=[C:4]([O:13][CH3:14])[CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 27550754-Hydroxy-2-methoxybenzenepropanoic acid

Product 1

HCID 21638546HCID 21638546, compound

Procedure

To a stirring solution of 3-[4-hydroxy-2-(methyloxy)phenyl]propanoic acid (229 mg, 1.17 mmol) in EtOH (14 mL) was added concentrated H2SO4 (0.031 mL, 0.58 mmol) and the reaction heated at reflux under nitrogen for 1 h. The mixture was then cooled to ambient temperature poured into ice (ca. 30 mL) and saturated aqueous Na2CO3 (60 mL) added. The mixture was then extracted with EtOAc (2×50 mL) and the combined organic layer washed with brine (70 mL) and concentrated under vacuum. The residue was then purified by SPE (silica, 5 g cartridge) eluting with cyclohexane:EtOAc (gradient 10:1 to 2:1) to afford the title compound (217 mg).

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux under nitrogen for 1 h
  3. additionadded
  4. extractionThe mixture was then extracted with EtOAc (2×50 mL)
  5. washthe combined organic layer washed with brine (70 mL)
  6. concentrationconcentrated under vacuum
  7. customThe residue was then purified by SPE (silica, 5 g cartridge)
  8. washeluting with cyclohexane

Sources & evidence

ORD record
ord-880d62f135c349149c7fdb79bed2d7a4
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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