4-Cyanobenzaldehyde → 4-(5-Octyl-1,3-dioxan-2-yl)benzonitrile

HRID 1197382Notes

Reaction equation

HRID 1197382 reaction equation
[CH2:1]([CH:9]([CH2:12][OH:13])[CH2:10][OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:14]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)#[N:15]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[CH2:1]([CH:9]1[CH2:10][O:11][CH:20]([C:19]2[CH:22]=[CH:23][C:16]([C:14]#[N:15])=[CH:17][CH:18]=2)[O:13][CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 660424-CyanobenzaldehydeHCID 3160622-Octylpropane-1,3-diol

Product 1

HCID 129249704-(5-Octyl-1,3-dioxan-2-yl)benzonitrileYield 72.9%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

In a 500-ml egg-plant type flask were put 32.3 g of 2-octyl-1,3-propanediol, 22.5 g of p-cyanobenzaldehyde, 0.11 g of p-toluenesulfonic acid monohydrate and 300 ml of benzene, and the mixture was heated. The generated water was removed by azeotropy with benzene. Then, benzene was distilled away, and the residue was neutralized with aqueous saturated sodium bicarbonate solution. The mixture was extracted with dichloromethane, and the extract was washed with water and then dried over anhydrous sodium sulfate. Dichloromethane was distilled away to give a solid which was then recrystallized from isooctane to give 37.7 g of colorless crystals.

Workup

  1. customIn a 500-ml egg-plant type flask were put
  2. customThe generated water was removed by azeotropy with benzene
  3. distillationThen, benzene was distilled away
  4. extractionThe mixture was extracted with dichloromethane
  5. washthe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationDichloromethane was distilled away
  8. customto give a solid which
  9. customwas then recrystallized from isooctane

Sources & evidence

ORD record
ord-daf636e4c66a4e9d81592295942da6d3
Source dataset
uspto-grants-1994_01
Patent number
US05275757

Reaction notes

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