4-Hydroxybenzaldehyde → 4-[2-(4-Formylphenoxy)ethyl]phenyl methyl sulfone

HRID 1595537Notes

Reaction equation

HRID 1595537 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21]O)=[CH:16][CH:15]=1)(=[O:13])=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1CCN(C(/N=N/C(N2CCCCC2)=O)=O)CC1>ClCCl>[CH3:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:16][CH:15]=1)(=[O:12])=[O:13]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 229884272-[4-(Methylsulfonyl)phenyl]-1-ethanol

Product 1

HCID 217049634-[2-(4-Formylphenoxy)ethyl]phenyl methyl sulfoneYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.83 g (15 mmole) 4-hydroxybenzaldehyde was dissolved in 35 ml dichloromethane under argon atmosphere. 1.5 g (7.5 mmole) 2-[4-(methylsulfonyl)phenyl]-1-ethanol was added followed by 3.93 g (15 mmole) triphenylphosphine and 3.78 g (15 mmole) 1,1-(azodicarbonyl)dipiperidine. The reaction mixture was stirred at room temperature and after 2 hours a precipitate is observed. The reaction was disrupted after 5 hours and the reaction mixture was filtered. The filtrate was purified by chromatography on silica gel using dichloromethane:methanol (98:2) as eluent giving 1.66 g (yield 54.5%) of 4-[2-(4-formylphenoxy)ethyl]phenyl methyl sulfone.

Workup

  1. waitThe reaction was disrupted after 5 hours
  2. filtrationthe reaction mixture was filtered
  3. customThe filtrate was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d9e0270f008c47be836fb733317b8c9e
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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