Pyridine → 5-(Chloromethyl)-1,2,3,4-tetrahydronaphthalene

HRID 1282919Notes

Reaction equation

HRID 1282919 reaction equation
[C:1]1([CH2:11]O)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.S(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][CH2:11][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 15562329(5,6,7,8-Tetrahydronaphthalen-1-yl)methanol

Product 1

HCID 3496875-(Chloromethyl)-1,2,3,4-tetrahydronaphthaleneYield 56%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

61 g (0.376 mol) of (5,6,7,8-tetrahydro-1-naphthyl)methanol with a purity of 78 % are dissolved in 450 ml of chloroform, in the presence of 35 g (0.38 mol) of pyridine. 90 ml of thionyl chloride in solution in 30 ml of chloroform are introduced dropwise and between 30 and 40°C into the solution which is obtained and this is heated under reflux for 6 hours. After partial evaporation of the chloroform and the thionyl chloride excess, washing is carried out with water and with a sodium bicarbonate solution, followed by drying over anhydrous sodium sulphate. Distillation of the oily residue permits the isolation of a liquid of boiling point b.p.0.5 = 81°-83°C, with a purity of 86 % (vapour phase chromatography), and this is taken up in 150 ml of hot hexane. The crystallisation is seeded by scratching with a glass rod. There are isolated 29.5 g of a product melting at 51°-52°C, with a yield of 56 % (theoretical yield = 53 g, depending on the degree of purity of the starting product). Vapour phase chromatography confirms a purity of 100 %.

Workup

  1. customis obtained
  2. temperaturethis is heated
  3. temperatureunder reflux for 6 hours
  4. customAfter partial evaporation of the chloroform
  5. washthe thionyl chloride excess, washing
  6. dry with materialby drying over anhydrous sodium sulphate
  7. distillationDistillation of the oily residue
  8. customb.p.0.5 = 81°-83°C
  9. customThe crystallisation

Sources & evidence

ORD record
ord-e49b1c2b9b4c49358245128f00c49c90
Source dataset
uspto-grants-1976_08
Patent number
US03973033

Reaction notes

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