Acetic Anhydride → 4-Butoxy-beta,beta-di(methylsulfonyl)styrene

HRID 1655112Notes

Reaction equation

HRID 1655112 reaction equation
[CH2:1]([O:5][C:6]1[CH:19]=[CH:18][C:9]([CH:10]=NC2C=CC=CC=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:20][S:21]([CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])(=[O:23])=[O:22].C(OC(=O)C)(=O)C>CC1C=CC(C)=CC=1>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:10]=[C:24]([S:25]([CH3:28])(=[O:27])=[O:26])[S:21]([CH3:20])(=[O:23])=[O:22])=[CH:18][CH:19]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 240586di(methylsulfonyl)methaneHCID 20077676N-(4-butoxybenzylidene)aniline

Product 1

HCID 200776734-Butoxy-beta,beta-di(methylsulfonyl)styreneYield 54.1%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2.5 g (0.01 mol) of N-(4-butoxybenzylidene)aniline, 1.9 g (0.011 mol) of di(methylsulfonyl) methane, 1.1 mL of acetic anhydride, and 60 mL of p-xylene were heated at 120° C. for 3 days. Upon cooling, the contents of the reaction were chromatographed on silica gel, using dichloromethane as the eluent. Crystallization from toluene afforded 1.8 g (54%) of (6) as a white solid.

Workup

  1. temperatureUpon cooling
  2. customthe contents of the reaction were chromatographed on silica gel
  3. customCrystallization from toluene

Sources & evidence

ORD record
ord-7e4e9a3cea324d93af09c4795be2e6d8
Source dataset
uspto-grants-1995_04
Patent number
US05410630

Reaction notes

Loading…