Hydrochloric Acid → [5-(4-Chlorophenyl)furan-2-yl](cyclopropyl)methanone

HRID 1658842Notes

Reaction equation

HRID 1658842 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH:5]1([C:8](Cl)=[O:9])[CH2:7][CH2:6]1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][CH:13]=1.Cl>C(=S)=S>[CH:5]1([C:8]([C:20]2[O:19][C:18]([C:15]3[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=3)=[CH:22][CH:21]=2)=[O:9])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 77637Cyclopropanecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10965101HCID 10965101, compound

Product 1

HCID 21525784[5-(4-Chlorophenyl)furan-2-yl](cyclopropyl)methanoneYield 17.3%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

To a stirring mixture of 128 g (0.96 mole) of AlCl3 and 720 ml of CS2 was added portionwise 100 g (0.96 mole) of cyclopropanecarboxylic acid chloride while keeping the temperature below 30° by means of an ice bath. A solution of 172 g (0.96 mole) of 2-(4-chlorophenyl)furan in 480 ml of CS2 was added dropwise while maintaining the temperature between 10°-15° with large volume of HCl gas being given off. The reaction mixture was stirred in an ice bath for 15 minutes, allowed to warm to room temperature over a one hour period, and then added to 2000 ml of ice/water. The aqueous layer was separated from the CS2 layer and extracted with 2 × 500 ml portions of CH2Cl2. The CS2 and CH2Cl2 layers were combined, were washed with 1000 ml of 6% Na2CO3 solution and with 1000 ml of water, and then dried over magnesium sulfate. The solvent was removed on a rotary evaporator leaving red-brown residue which was extracted several times with boiling hexane. The combined hexane extracts were cooled and the resulting solid filtered and air dried to yield 41 g (17%) of product. An analytical sample was prepared by recrystallizing a sample from hexane/Darco, m.p. 88°-89°.

Workup

  1. customthe temperature below 30°
  2. customThe aqueous layer was separated from the CS2 layer
  3. extractionextracted with 2 × 500 ml portions of CH2Cl2
  4. washwere washed with 1000 ml of 6% Na2CO3 solution and with 1000 ml of water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed on a rotary evaporator
  7. customleaving red-brown residue which
  8. extractionwas extracted several times with boiling hexane
  9. temperatureThe combined hexane extracts were cooled
  10. filtrationthe resulting solid filtered
  11. customair dried

Sources & evidence

ORD record
ord-d74bf5313806453eae37a64fd01d7571
Source dataset
uspto-grants-1976_06
Patent number
US03966771

Reaction notes

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