Thionyl Chloride → Methyl 1-chloroindan-4-carboxylate

HRID 436157

Reaction equation

HRID 436157 reaction equation
O[CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH2:4][CH2:3]1.S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[Cl:17][CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20310103Methyl 1-hydroxyindan-4-carboxylate

Product 1

HCID 20310089Methyl 1-chloroindan-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 6 ml. of chloroform is dissolved 5.7 g. of methyl 1-hydroxyindan-4-carboxylate and, under cooling with ice, the solution is stirred. Then, 3 ml. of thionyl chloride is added dropwise and, after the dropwise addition has been completed, the mixture is further stirred under cooling with ice for one hour. Then, the solvent and the excess thionyl chloride are distilled off under reduced pressure. The residue obtained is purified by column chromatography on silica gel (500 g. silica gel; eluant: chloroform). The procedure gives methyl 1-chloroindan-4-carboxylate as an oily product.

Workup

  1. additionafter the dropwise addition
  2. stirringthe mixture is further stirred
  3. temperatureunder cooling with ice for one hour
  4. distillationThen, the solvent and the excess thionyl chloride are distilled off under reduced pressure
  5. customThe residue obtained
  6. customis purified by column chromatography on silica gel (500 g. silica gel; eluant: chloroform)

Sources & evidence

ORD record
ord-2dd858b351e64e139b66392a4ae5f5aa
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Linked notes

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