Sodium Chloride → HCID 178444423, compound

HRID 1090603Notes

Reaction equation

HRID 1090603 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]CCCC)=[C:16]([C:25]#[N:26])[C:15]=2[C:27]#[N:28])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+]>O>[C:25]([C:16]1[C:15]([C:27]#[N:28])=[C:14]([CH2:13][CH2:12][C@H:9]2[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]2)[CH:19]=[CH:18][C:17]=1[OH:20])#[N:26]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 178444422HCID 178444422, compound

Product 1

HCID 178444423HCID 178444423, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A finely powdered mixture was prepared from 2.2 g of 2-(trans-4-pentylcyclohexyl)-1-(2,3-dicyano-4-butyloxyphenyl)ethane, 1.4 g of anhydrous aluminium chloride and 0.3 g of sodium chloride and this mixture was heated to 150° C. on an oil-bath for 40 minutes under anhydrous conditions. The cooled mixture was treated with 250 ml of water and extracted three times with 50 ml of dichloromethane each time. The combined organic phases were washed with 250 ml of water, dried over magnesium sulphate and concentrated. Chromatography of the residue on silica gel with toluene/ethyl acetate (vol. 4:1) gave 0.6 g of 2,3-dicyano-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenol; m.p. 100°-102° C.

Workup

  1. extractionextracted three times with 50 ml of dichloromethane each time
  2. washThe combined organic phases were washed with 250 ml of water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3761ba68e21f4f6d990ebaf55ffa8f47
Source dataset
uspto-grants-1992_01
Patent number
US05082589

Reaction notes

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