Water → 1-(2,3-Dihydro-5-benzofuranyl)ethanone

HRID 2406842Notes

Reaction equation

HRID 2406842 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:10](OC(=O)C)(=[O:12])[CH3:11].O>[Cl-].[Zn+2].[Cl-].ClCCl>[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1)(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 10329Dihydrobenzofuran

Product 1

HCID 1452201-(2,3-Dihydro-5-benzofuranyl)ethanoneYield 24.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 44.4 g (0.37 moles) of 2,3-dihydrobenzofuran and 37.8 g (0.37 moles) of acetic anhydride were added with 5.0 g (37 mmoles) of anhydrous zinc chloride. The mixture was heated to 95-105° C. for 10 hrs; after cooling to room temperature the mixture is added with 50 ml of water and 50 ml of dichloromethane. The organic phase was separated and the aqueous phase was extracted twice with dichloromethane (2× 30 ml). The organic phases were collected together, and washed with 50 ml of a saturated aqueous solution of sodium carbonate. The organic phase was separated and evaporated u.v. (20° C./21 mbar). The residue was then distilled at 99-100° C./0.08 mbar obtaining 14.5 g (0.089 moles) of 5-acetyl-2,3-dihydrobenzofuran.

Workup

  1. temperatureafter cooling to room temperature the mixture
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted twice with dichloromethane (2× 30 ml)
  4. customThe organic phases were collected together
  5. washwashed with 50 ml of a saturated aqueous solution of sodium carbonate
  6. customThe organic phase was separated
  7. customevaporated u.v
  8. custom(20° C./21 mbar)
  9. distillationThe residue was then distilled at 99-100° C./0.08 mbar

Sources & evidence

ORD record
ord-cd74736b70f944cbb3b300e6fbfac7b8
Source dataset
uspto-grants-2014_08
Patent number
US08809389B2

Reaction notes

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