Dimethyl Sulfoxide → HCID 178444315, compound

HRID 1589610Notes

Reaction equation

HRID 1589610 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:19]=[CH:18][C:15]([CH2:16]O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].P(Cl)(Cl)Cl.[C-:24]#[N:25].[Na+].CS(C)=O>O>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:19]=[CH:18][C:15]([CH2:16][C:24]#[N:25])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 24387Phosphorus trichlorideHCID 178444336HCID 178444336, compound

Product 1

HCID 178444315HCID 178444315, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

27.9 g of 4-(trans-4-pentylcyclohexyl)benzyl chloride (obtained by chloromethylation of trans-4-pentyl-1-phenylcyclohexane or by esterification of 4-(trans-4-pentylcyclohexyl)benzoic acid, reduction of the methyl or ethyl ester obtained to give 4-(trans-4-pentylcyclohexyl)benzyl alcohol and reaction with PCl3) was added within 15 minutes at 60°, with stirring, to a mixture of 5.5 g of NaCN and 40 ml of dimethyl sulfoxide. The mixture was heated at 70° for 6 hours, cooled down, poured into water and 4-(trans-4-pentylcyclohexyl)phenylacetonitrile was obtained, m.p. 53°, c.p. -19°.

Workup

  1. customobtained
  2. customto give
  3. additionwas added within 15 minutes at 60°
  4. temperatureThe mixture was heated at 70° for 6 hours
  5. temperaturecooled down

Sources & evidence

ORD record
ord-4ad0c404c9aa4c20a68367463c95e338
Source dataset
uspto-grants-1986_02
Patent number
US04572794

Reaction notes

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