Sulfuryl chloride → 4-Chloro-5,6,7,8-tetrahydronaphthalen-1-ol

HRID 1076871

Reaction equation

HRID 1076871 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:15])(=O)=O>C(Cl)(Cl)(Cl)Cl>[Cl:15][C:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:1]([OH:11])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 682585,6,7,8-Tetrahydro-1-naphthol

Product 1

HCID 202033334-Chloro-5,6,7,8-tetrahydronaphthalen-1-olYield 17.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 37 grams (0.25 mole) of 5,6,7,8-tetrahydronaphthol in 200 ml of carbon tetrachloride was treated dropwise with stirring with 33.8 grams (0.25 mole) of sulfuryl chloride at room temperature. When addition was complete the reaction mixture slowly brought to boiling over a 1 hour period and held there at reflux for 30 minutes. After cooling to ambient temperature the reaction mixture was washed with 10 percent aqueous sodium carbonate and then with water. After drying over calcium chloride the carbon tetrachloride solution was distilled to give a portion, b.p. 110-112/0.25 mm, which was recrystallized from hexane to give 8 grams (17.5 percent) of product, m.p. 58°-59°C.

Workup

  1. additionWhen addition
  2. temperatureat reflux for 30 minutes
  3. washwas washed with 10 percent aqueous sodium carbonate
  4. dry with materialAfter drying over calcium chloride the carbon tetrachloride solution
  5. distillationwas distilled
  6. customto give a portion
  7. custom110-112/0.25 mm, which was recrystallized from hexane

Sources & evidence

ORD record
ord-08e7a9c04ba34703be6b3f2656ea7360
Source dataset
uspto-grants-1976_05
Patent number
US03958006

Linked notes

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