Potassium Carbonate → HCID 178444589, compound

HRID 653380Notes

Reaction equation

HRID 653380 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([CH:9]=[O:10])[CH2:5][CH2:4]1)#[N:2].[CH2:11]([CH:16]([CH2:19]O)[CH2:17][OH:18])[CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:11]([C@@H:16]1[CH2:17][O:18][C@@H:9]([C@H:6]2[CH2:7][CH2:8][C@H:3]([C:1]#[N:2])[CH2:4][CH2:5]2)[O:10][CH2:19]1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1175092-Pentyl-1,3-propanediolHCID 178511250HCID 178511250, compound

Product 1

HCID 178444589HCID 178444589, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 2.00 g of trans-4-cyanocyclohexanecarboxaldehyde, 2.13 g of 2-pentyl-1,3-propanediol and 65 mg of p-toluenesulphonic acid in 100 ml of benzene was heated to reflux for 3 hours while gassing with argon and with separation of water in a round flask provided with a water separator and a reflux condenser. The mixture was subsequently treated with 3.0 g of potassium carbonate, stirred at room temperature for 16 hours, then filtered and the filtrate was concentrated. Recrystallization of the crystalline residue (4.1 g) from hexane at 0° C. gave 1.47 g (38%) of trans-4-(trans-5-pentyl-m-dioxan-2-yl)cyclohexanecarbonitrile as colourless crystals in a purity of 99.1%. After a further recrystallization from hexane at 0° C., the purity increased to 99.9%; m.p. (C--N) 45.6° C., cl.p. (N--I) 46.7° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. customwhile gassing with argon and with separation of water in a round flask
  4. customprovided with a water separator and a reflux condenser
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customRecrystallization of the crystalline residue (4.1 g) from hexane at 0° C.

Sources & evidence

ORD record
ord-44f6b8b15e604beba441580bd7b63ac1
Source dataset
uspto-grants-1987_06
Patent number
US04676604

Reaction notes

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