Ethanol → Ethyl 2,3-Dihydrobenzofuran-5-ylacetate

HRID 868621Notes

Reaction equation

HRID 868621 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([OH:13])=[O:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:14]1(C)C=CC=C[CH:15]=1.C(O)C.S(=O)(=O)(O)O>O.C(OCC)(=O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1140TolueneHCID 27374552,3-Dihydro-5-benzofuranacetic acid

Product 1

HCID 13704383Ethyl 2,3-Dihydrobenzofuran-5-ylacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22728543Water ethylacetateSolvent

Procedure

2,3-dihydrobenzofuran-5-ylacetic acid (5.4 g) was heated at reflux in a solution of toluene (200 ml), ethanol (20 ml) and concentrated sulfuric acid (0.5 ml) with the azeotropic removal of water. When the reaction was complete, approximately 6 hours, the mixture was added to water/ethyl acetate and extracted with ethyl acetate. The organic extracts were combined and washed with 10% sodium carbonate, dried over sodium sulfate and the solvent evaporated to give the title compound as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with 10% sodium carbonate
  3. dry with materialdried over sodium sulfate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-995e1e9946c646fb8a03efc05e7ac0b9
Source dataset
uspto-grants-1988_10
Patent number
US04780480

Reaction notes

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