Methanol → HCID 12740032, compound

HRID 648121Notes

Reaction equation

HRID 648121 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:3]1=2.S(Cl)(Cl)=O.[CH3:26]O>>[CH3:26][O:1][C:2]1[C:3]2[CH:16]=[C:15]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:14]=[CH:13][C:4]=2[CH2:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 12902573HCID 12902573, compound

Product 1

HCID 12740032HCID 12740032, compound

Procedure

In 50 ml of dry methanol was dissolved 6.3 g of methyl 10,11-dihydro-11-oxo-5H-dibenzo[a,d]cycloheptene-2-acetate obtained in Example 10. Thionyl chloride (7 g) was added, and the solution was heated under reflux for 2 hours with stirring. After the reaction, the reaction mixture was cooled, and methanol was distilled off. The residue was dissolved in 200 ml of benzene. The benzene solution was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The benzene was then distilled off. The residue was chromatographed on a silica gel column using benzene as an eluent. A slightly yellow solid was obtained from the eluate. Recrystallization from n-hexane afforded 4.6 g of methyl 11-methoxy-5H-dibenzo[a,d]cycloheptene-2-acetate as colorless needle-like crystals having a melting point of 72° to 73° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter the reaction
  4. temperaturethe reaction mixture was cooled
  5. distillationmethanol was distilled off
  6. dissolutionThe residue was dissolved in 200 ml of benzene
  7. washThe benzene solution was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe benzene was then distilled off
  10. customThe residue was chromatographed on a silica gel column
  11. customA slightly yellow solid was obtained from the eluate
  12. customRecrystallization from n-hexane

Sources & evidence

ORD record
ord-ac0d51c0a85c473baabd6e67197661e3
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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