Hydrochloric Acid → 2,3,4,5-Tetrahydro-1-benzoxepin-5-one

HRID 1613605Notes

Reaction equation

HRID 1613605 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>ClCCCl>[O:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 788194-Phenoxybutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3155752,3,4,5-Tetrahydro-1-benzoxepin-5-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 238 g (1.2 mole) of 4-phenoxybutyryl chloride, dissolved in 350 ml of 1,2-dichloroethane, is added dropwise to a suspension, cooled to 0° C., of 192 g of aluminum trichloride in 1,200 ml of 1,2-dichloroethane within 4.5 hours while passing through nitrogen and stirring vigorously. The mixture is then stirred at 0° C. for 1.5 hours and allowed to warm to room temperature overnight. The mixture is added to a stirred mixture of 2,000 ml of concentrated hydrochloric acid and 2.5 kg of ice and then stirred for 1.5 hours. The aqueous phase is decanted off, and insoluble residue is removed from the organic phase by filtration, washing thoroughly with 1,2-dichloroethane. The aqueous phase is extracted 3-4 times more with methylene chloride, and the combined organic phases are washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution and dried over sodium sulfate. A yellowish oil is obtained after the solvent has been evaporated off in vacuo and is dissolved in diethyl ether, and the last residues of dyestuff are removed by filtration. Evaporation in vacuo results in a clear oil which distils at 74°-75° C./0.02 torr.

Workup

  1. additionis added dropwise to a suspension
  2. stirringThe mixture is then stirred at 0° C. for 1.5 hours
  3. stirringstirred for 1.5 hours
  4. customThe aqueous phase is decanted off
  5. custominsoluble residue is removed from the organic phase by filtration
  6. washwashing thoroughly with 1,2-dichloroethane
  7. extractionThe aqueous phase is extracted 3-4 times more with methylene chloride
  8. washthe combined organic phases are washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. customA yellowish oil is obtained after the solvent
  11. customhas been evaporated off in vacuo
  12. dissolutionis dissolved in diethyl ether
  13. customthe last residues of dyestuff are removed by filtration
  14. customEvaporation in vacuo
  15. customresults in a clear oil which
  16. customdistils at 74°-75° C./0.02 torr

Sources & evidence

ORD record
ord-d00fa4c71b1d452dbb9c2d3fc949bb2e
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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