Ethanol → HCID 22228634, compound

HRID 1744284Notes

Reaction equation

HRID 1744284 reaction equation
[OH:1][C:2]1[C:14]([CH3:15])=[CH:13][C:5]2[C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][O:8][C:4]=2[C:3]=1[CH3:16].[CH2:17](O)[CH3:18]>S(=O)(=O)(O)O>[OH:1][C:2]1[C:14]([CH3:15])=[CH:13][C:5]2[C:6]([CH2:9][C:10]([O:12][CH2:17][CH3:18])=[O:11])=[CH:7][O:8][C:4]=2[C:3]=1[CH3:16]

Participants

4

Reactant 2

HCID 702EthanolHCID 22228629HCID 22228629, compound

Product 1

HCID 22228634HCID 22228634, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3.1 g (14 mmol) of 2-(6-hydroxy-5,7-dimethyl-1-benzofuran-3-yl) acetic acid are heated at reflux overnight in 1.72 ml of conc. sulfuric acid in 861 ml of ethanol. The mixture is concentrated down to 50 ml and then diluted with water and ethyl acetate; the phases are separated and the aqueous phase is extracted with ethyl acetate. The combined phases are washed with a saturated solution of NaCl, dried over sodium sulfate and concentrated. Chromatographic purification (dichloromethane) yields 2.6 g (75%) of ethyl 2-(6-hydroxy-5,7-dimethyl-1-benzofuran-3-yl)acetate.

Workup

  1. concentrationThe mixture is concentrated down to 50 ml
  2. additiondiluted with water and ethyl acetate
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. washThe combined phases are washed with a saturated solution of NaCl
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customChromatographic purification (dichloromethane)

Sources & evidence

ORD record
ord-f4752146e35942bb956841698b053ab6
Source dataset
uspto-grants-2006_03
Patent number
US07015246B2

Reaction notes

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