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

HRID 868618Notes

Reaction equation

HRID 868618 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-]>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

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10329Dihydrobenzofuran2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 1452201-(2,3-Dihydro-5-benzofuranyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of 2,3-dihydrobenzofuran (5.0 g) in dichloromethane (30 ml) at -10° C. was slowly added a solution of acetyl chloride (5.9 ml) and anhydrous aluminum chloride (5.5 g) in dichloromethane (30 ml) while keeping the temperature below -6° C. After addition of the 2,3-dihydrobenzofuran was completed, the reaction mixture was stirred for 10 minutes at -10° C. The reaction mixture was then added to an ice/hydrochloric acid mixture which was extracted with dichloromethane. The combined dichloromethane extracts were washed with water and dilute sodium hydroxide, the organic layer dried over sodium sulfate and evaporated. The resulting residue was recrystallized from hexane to give 5-acetyl-2,3-dihydrobenzofuran, m.p.--56°-57° C.

Workup

  1. customthe temperature below -6° C
  2. extractionwas extracted with dichloromethane
  3. washThe combined dichloromethane extracts were washed with water and dilute sodium hydroxide
  4. dry with materialthe organic layer dried over sodium sulfate
  5. customevaporated
  6. customThe resulting residue was recrystallized from hexane

Sources & evidence

ORD record
ord-af3e1dda15c1499f95c5154638e8ae5b
Source dataset
uspto-grants-1988_10
Patent number
US04780480

Reaction notes

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