1,2,3,4-Tetrahydro-1-naphthalenol → 1-Chloro-1,2,3,4-tetrahydronaphthalene

HRID 542856

Reaction equation

HRID 542856 reaction equation
[CH:1]1(O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:14])=O>C(Cl)(Cl)Cl.N1C=CC=CC=1>[Cl:14][CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 107231,2,3,4-Tetrahydro-1-naphthalenolHCID 24386Thionyl Chloride

Product 1

HCID 1887171-Chloro-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

One hundred grams of 1,2,3,4-tetrahydro-1-naphthol were dissolved in 1 liter of chloroform and 53.9 ml of pyridine. The mixture was cooled with an external ice bath and 98.6 ml of thionyl chloride were added over a 1 hour period. The reaction mixture was stirred an additional 2 hours with cooling, concentrated in vacuo, and the residue taken up in 1 liter of methylene chloride. The methylene chloride solution was washed with water, a 5% sodium bicarbonate solution, water again, dried over sodium sulfate, and evaporated to dryness to provide the desired intermediate 1,2,3,4-tetrahydro-1-chloronaphthalene.

Workup

  1. temperatureThe mixture was cooled with an external ice bath
  2. temperaturewith cooling
  3. concentrationconcentrated in vacuo
  4. washThe methylene chloride solution was washed with water
  5. dry with materiala 5% sodium bicarbonate solution, water again, dried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-ba7cb3b3a3a74618903faef23802b1b6
Source dataset
uspto-grants-1987_04
Patent number
US04659730

Linked notes

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