Sulfuric Acid → HCID 178454711, compound

HRID 894378Notes

Reaction equation

HRID 894378 reaction equation
[OH:1][CH2:2][CH2:3][N:4]=[C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][C:8]=1[C:17]([OH:19])=[O:18])[OH:6].[C:20](O)(=[O:24])[C:21]([CH3:23])=[CH2:22].S(=O)(=O)(O)O.C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.[OH-].[Ca+2].[OH-]>C1(C)C=CC=CC=1.O>[C:20]([O:1][CH2:2][CH2:3][N:4]=[C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][C:8]=1[C:17]([OH:19])=[O:18])[OH:6])(=[O:24])[C:21]([CH3:23])=[CH2:22]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 4093Methacrylic AcidHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 6093208Calcium HydroxideHCID 178524635HCID 178524635, compound

Product 1

HCID 178454711HCID 178454711, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

24.3 g (0.1 mol) of N-(2'-hydroxyethyl)-3,4-dihydronaphthalene-1,2-dicarboxylic acid imide, 12.9 g (0.15 mol) of methacrylic acid, 1.6 ml of concentrated sulphuric acid and 1.0 g of 2,6-di-tert.-butyl-p-cresol are dissolved in toluene and the solution is refluxed for 2 hours, the water formed being separated off by means of a water separator downstream of the reaction vessel. The reaction solution is then cooled to room temperature, 5.52 g (0.075 mol) of calcium hydroxide are added and the mixture is stirred thoroughly for 5 minutes. After filtering, the filtrate is concentrated to dryness in vacuo at 60° C. This yields 28.8 g (95.7% of theory) of N-(2'-methacryloyloxyethyl)-3,4-dihydronaphthalene-1,2-dicarboxylic acid imide.

Workup

  1. temperaturethe solution is refluxed for 2 hours
  2. custombeing separated off by means of a water separator downstream of the reaction vessel
  3. filtrationAfter filtering
  4. concentrationthe filtrate is concentrated to dryness in vacuo at 60° C

Sources & evidence

ORD record
ord-50c9ecd11a944770934da887a5394828
Source dataset
uspto-grants-1981_08
Patent number
US04283509

Reaction notes

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