4-Hydroxybenzaldehyde → 4-[2-(4-Methylmercaptophenyl)ethoxy]benzaldehyde

HRID 1595533Notes

Reaction equation

HRID 1595533 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1CCN(C(/N=N/C(N2CCCCC2)=O)=O)CC1.O[C:50]1[CH:57]=[CH:56][C:53]([CH:54]=[O:55])=[CH:52][CH:51]=1>ClCCl>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:50]2[CH:57]=[CH:56][C:53]([CH:54]=[O:55])=[CH:52][CH:51]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 27600862-(4-Methylsulfanylphenyl)ethanolHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)

Product 1

HCID 537815244-[2-(4-Methylmercaptophenyl)ethoxy]benzaldehydeYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.7 g (10 mmole) 2-[4-(methylsulfanyl)phenyl]-1-ethanol, 5.24 g (20 mmole) triphenylphosphine and 5.05 g (20 mmole) 1,1-(azodicarbonyl)dipiperidine was added to a mixture of 2.47 g (20 mmole) 4-hydroxybenzaldehyde in 40 ml dichloromethane under argon atmosphere. Stirring at room temperature for 2 hours, (more dichloromethane was added after 20 minutes), gave a solid material that was removed by filtration. The filtrate was purified by chromatography on silica gel using dichloromethane as eluent to give 2.3 g (yield 84.4%) of 4-[2-(4-methylmercaptophenyl)ethoxy]benzaldehyde.

Workup

  1. customgave a solid material that
  2. customwas removed by filtration
  3. customThe filtrate was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d5bf3b81f6b5458190c07a4d59e5b482
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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