Thionyl Chloride → 9-Methyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

HRID 894189Notes

Reaction equation

HRID 894189 reaction equation
[O:1]([CH2:8][C:9]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O>C1C=CC=CC=1>[CH3:18][C:15]1[CH:16]=[CH:17][C:9]2[CH2:8][O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=3[C:11](=[O:13])[C:10]=2[CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 211627312-Phenoxymethyl-5-methylbenzoic Acid

Product 1

HCID 211627129-Methyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Mix 0.2 gm of the phenoxymethylbenzoic acid of Step A, 1 ml of thionyl chloride and 10 ml of dry benzene. Reflux for 1 hour and concentrate to dryness in vacuo. Dissolve the residue in 10 ml of dry 1,2-dichloroethane and add 0.3 gm of anhydrous aluminum chloride while stirring in an ice bath. After 10 minutes, pour the reaction mixture into ice water, extract with chloroform, wash with water and dry over magnesium sulfate. Concentrate to dryness and chromatograph the residue over silica gel eluting with chloroform. Concentrate the eluate to dryness and crystallize from hexane to obtain the title product.

Workup

  1. temperatureReflux for 1 hour
  2. concentrationconcentrate to dryness in vacuo
  3. dissolutionDissolve the residue in 10 ml of dry 1,2-dichloroethane
  4. additionadd 0.3 gm of anhydrous aluminum chloride
  5. additionpour the reaction mixture into ice water
  6. extractionextract with chloroform
  7. washwash with water
  8. dry with materialdry over magnesium sulfate
  9. concentrationConcentrate to dryness and chromatograph the residue over silica gel eluting with chloroform
  10. concentrationConcentrate the eluate to dryness
  11. customcrystallize from hexane

Sources & evidence

ORD record
ord-af7796aadce34e76b8bb53888f005b13
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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