Thionyl Chloride → HCID 20310099, compound
Reaction equation
[C:1]([CH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([OH:14])=O)[C:6]=2[CH2:5][CH2:4]1)#[N:2].S(Cl)([Cl:17])=O>>[C:1]([CH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([Cl:17])=[O:14])[C:6]=2[CH2:5][CH2:4]1)#[N:2]Participants
Procedure
To 6.0 g. of 1-cyanoindan-4-carboxylic acid is added 96 ml. of thionyl chloride and the mixture is allowed to stand at room temperature for 14 hours. The excess thionyl chloride is removed under reduced pressure. To 1-cyanoindan-4-carbonylchloride, which is thus obtained as the residue, are added 50 ml. of toluene and 50 ml. of methylene chloride, followed by the addition of 6.0 g. of anhydrous aluminum chloride. The mixture is stirred at room temperature for 1 hour. After cooling, the reaction product is poured into ice-hydrochloric acid and extracted with ether. The extract is washed with 1N hydrochloric acid and a saturated aqueous solution of sodium chloride, followed by drying. The solvent is distilled off under reduced pressure and the residue is purified by column chromatography on silica gel (500 g. silica gel; eluted with chloroform). The procedure gives 4-(p-toluoyl)indan-1-carbonitrile as an oily product.
Workup
- customThe excess thionyl chloride is removed under reduced pressure
Sources & evidence
- ORD record
- ord-e52233664b3b48cc8d3788edd5767407
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04111997
Reaction notes
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