Thionyl Chloride → Methyl 1-chloroindan-4-carboxylate

HRID 1606721Notes

Reaction equation

HRID 1606721 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>>[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

3

Reactant 2

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

Product 1

HCID 20310089Methyl 1-chloroindan-4-carboxylate

Procedure

In 6 ml. of chllroform 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. dissolutionof chllroform is dissolved 5.7 g
  2. additionafter the dropwise addition
  3. stirringthe mixture is further stirred
  4. temperatureunder cooling with ice for one hour
  5. distillationThen, the solvent and the excess thionyl chloride are distilled off under reduced pressure
  6. customThe residue obtained
  7. customis purified by column chromatography on silica gel (500 g. silica gel; eluant: chloroform)

Sources & evidence

ORD record
ord-49d482482cf3431abc7d24e93cc534d1
Source dataset
uspto-grants-1976_04
Patent number
US03953500

Reaction notes

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