4-Cyanobenzaldehyde → HCID 19105707, compound

HRID 1197384Notes

Reaction equation

HRID 1197384 reaction equation
C(OC(CO)CO)CCCCCCC.C(C1C=CC(C=O)=CC=1)#N.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:37]([O:45][CH2:46][CH:47]1[CH2:51][O:50][CH:49]([C:52]2[CH:59]=[CH:58][C:55]([C:56]#[N:57])=[CH:54][CH:53]=2)[O:48]1)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>C1C=CC=CC=1>[CH2:37]([O:45][CH:46]1[CH2:47][O:48][CH:49]([C:52]2[CH:53]=[CH:54][C:55]([C:56]#[N:57])=[CH:58][CH:59]=2)[O:50][CH2:51]1)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 4

HCID 660424-CyanobenzaldehydeHCID 3724412-Octyl glyceryl etherHCID 521998p-Toluenesulfonic acid monohydrateHCID 19105708HCID 19105708, compound

Product 1

HCID 19105707HCID 19105707, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 10.2 g of the diol mixture obtained in (1) were added 100 ml of benzene, 6.6 g of p-cyanobenzaldehyde and p-toluenesulfonic acid monohydrate, and the mixture was heated. The generated water was removed by azeotropy with benzene. Then, the remaining benzene was distilled away, 200 ml of aqueous saturated sodium bicarbonate solution was added to the residue, and the mixture was extracted with dichloromethane. The extract was washed twice with water and dried over anhydrous sodium sulfate, and the solvent was distilled away to give 15.5 g of a crude product containing a by-product 4-(4-octyloxymethyl-1,3-dioxolan-2-yl)benzonitrile. This crude product was treated by column chromatography using silica gel to give 1.4 g of the desired product.

Workup

  1. temperaturethe mixture was heated
  2. customThe generated water was removed by azeotropy with benzene
  3. distillationThen, the remaining benzene was distilled away
  4. addition200 ml of aqueous saturated sodium bicarbonate solution was added to the residue
  5. extractionthe mixture was extracted with dichloromethane
  6. washThe extract was washed twice with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled away
  9. customto give 15.5 g of a crude product

Sources & evidence

ORD record
ord-9d9269bff7aa4c2685e0a90aac2317df
Source dataset
uspto-grants-1994_01
Patent number
US05275757

Reaction notes

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