Hydrochloric Acid → 5-chloro-3-methylthio-5H-dibenzo[a,d]cycloheptene

HRID 2071745Notes

Reaction equation

HRID 2071745 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[CH:8](O)[C:7]=2[CH:18]=1.[ClH:19]>O1CCOCC1>[Cl:19][CH:8]1[C:7]2[CH:18]=[C:3]([S:2][CH3:1])[CH:4]=[CH:5][C:6]=2[CH:12]=[CH:11][C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 202322443-methylthio-5H-dibenzo[a,d]cyclohepten-5-ol

Product 1

HCID 202322695-chloro-3-methylthio-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 18 g. (0.071 mole) of 3-methylmercapto-5H-dibenzo[a,d]cyclohepten-5-ol in 90 ml. of dry dioxane is cooled in an ice-bath and saturated with dry hydrogen chloride. A solid separates and when precipitation appears to be complete, the mixture is stirred with 150 ml. of petroleum ether and the product collected, washed with petroleum ether, and dried in a vacuum desiccator over potassium hydroxide. The yield of 5-chloro-3-methylmercapto-5H-dibenzo[a,d]cycloheptene is 16 g. (84%), m.p. 135°-138° C. The melting point is unchanged by recrystallization from cyclohexane.

Workup

  1. customA solid separates and when precipitation
  2. customof petroleum ether and the product collected
  3. washwashed with petroleum ether
  4. dry with materialdried in a vacuum desiccator over potassium hydroxide
  5. customThe melting point is unchanged by recrystallization from cyclohexane

Sources & evidence

ORD record
ord-f1e1ba1c875c4bf2a20976e1f687871e
Source dataset
uspto-grants-1977_09
Patent number
US04048223

Reaction notes

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