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

HRID 1284258Notes

Reaction equation

HRID 1284258 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-b64f063806d140d483ea25af6f6387d1
Source dataset
uspto-grants-1976_08
Patent number
US03978121

Reaction notes

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