Hydrochloric Acid → trans-2-p-Cyanophenyl-5-pentyl-1,4-dioxane

HRID 845011Notes

Reaction equation

HRID 845011 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][O:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[C:19](C#N)#[N:20].N1C=CC=CC=1.Cl>CN1CCCC1=O>[C:19]([C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][O:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][O:9]2)=[CH:4][CH:3]=1)#[N:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 9999CyanogenHCID 86742258trans-2-p-Bromophenyl-5-pentyl-1,4-dioxane

Product 1

HCID 86742257trans-2-p-Cyanophenyl-5-pentyl-1,4-dioxane

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 31.3 g. trans-2-p-bromophenyl-5-pentyl-1,4-dioxane, 10 g. Cu2 (CN)2, 120 ml. pyridine and 60 ml. N-methylpyrrolidone is heated for 2 hours to 150°. One cools, adds thereto a solution of 120 g. FeCl3.6H2O in 600 ml. 20% hydrochloric acid, heats to 70° for 1.5 hours, while stirring. Works up as usu 1 and obtains trans-2-p-cyanophenyl-5-pentyl-1,4-dioxane.

Workup

  1. additionA mixture of 31.3 g
  2. additionadds

Sources & evidence

ORD record
ord-7710397969054b5c91874984c6919d8f
Source dataset
uspto-grants-1988_07
Patent number
US04755323

Reaction notes

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