Thionyl Chloride → Methyl 1-chloroindan-4-carboxylate

HRID 1763422Notes

Reaction equation

HRID 1763422 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-5c52c6d286014d4bb5165b68d9ff3572
Source dataset
uspto-grants-1978_09
Patent number
US04111997

Reaction notes

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