4-Hydroxybenzaldehyde → 4-[2-(4-Formylphenoxy)ethyl]benzonitrile

HRID 987336Notes

Reaction equation

HRID 987336 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:47]([C:49]1[CH:57]=[CH:56][C:52]([CH2:53][CH2:54]O)=[CH:51][CH:50]=1)#[N:48]>ClCCl.CCCCCCC>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:54][CH2:53][C:52]2[CH:56]=[CH:57][C:49]([C:47]#[N:48])=[CH:50][CH:51]=2)=[CH:3][CH:4]=1)=[O:7]

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 28008154-(2-Hydroxyethyl)benzonitrile

Product 1

HCID 229887784-[2-(4-Formylphenoxy)ethyl]benzonitrileYield 35.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8900HeptaneSolvent

Procedure

p-Hydroxybenzaldehyde (24.9 g; 203.8 mmole) was dissolved in dichloromethane (dry). ADDP (47.2 g; 187 mmole) was added followed by addition of triphenylphosphine (49 g; 187 mmole). The reaction mixture was stirred at room temperature for 45 minutes and then p-cyanophenethyl alcohol (25 g; 110 mmole) dissolved in a small amount of dichloromethane (dry) was added in portions during one hour. The reaction mixture was stirred at room temperature over night, filtered and evaporated. Chromatography of the residue on silica gel using ethyl acetate:heptane as eluant gave 9.7 g (22.7% yield) of 4-[2-(4-formylphenoxy)ethyl]benzonitrile.

Workup

  1. additionwas added in portions during one hour
  2. stirringThe reaction mixture was stirred at room temperature over night
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ac8806ac24f042a1aa1a505f2ae62acf
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

Loading…