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

HRID 1690140Notes

Reaction equation

HRID 1690140 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](Cl)(=[O:12])[CH3:11].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:12])[CH3:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 10329DihydrobenzofuranHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1452201-(2,3-Dihydro-5-benzofuranyl)ethanoneYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

2,3-Dihydrobenzofuran (10 g, 83.2 mmol) was dissolved in dichloromethane (400 mL). The resultant mixture was added sequentially with acetyl chloride (11.8 mL, 167 mmol) and aluminum chloride (33.3 g, 250 mmol) at −10° C., and stirred at −10° C. for 0.5 hour. The reaction solution was added with 5% aqueous solution of hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. 1-(2,3-Dihydrobenzofuran-5-yl)ethanone (13.4 g, yield 99%) was obtained as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5880c24f4fb445da2bc0a5d577d1241
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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