Resorcinol, monobenzoate → HCID 20281011, compound

HRID 463529Notes

Reaction equation

HRID 463529 reaction equation
[C:1]([O:9][C:10]1[CH:16]=[CH:15][CH:14]=[C:12]([OH:13])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:22][CH2:23][CH2:24][N:25]=[C:26]=[O:27])(=[O:21])[C:18]([CH3:20])=[CH2:19]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C(Cl)(Cl)Cl>[C:17]([O:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[O:13][C:12]1[CH:14]=[CH:15][CH:16]=[C:10]([O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:11]=1)(=[O:21])[C:18]([CH3:20])=[CH2:19]

Participants

5

Reactant 2

HCID 8690Resorcinol, monobenzoateHCID 354092-Isocyanatoethyl methacrylate

Product 1

HCID 20281011HCID 20281011, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 65 grams (0.30 mol) of resorcinol monobenzoate, 50 grams (0.32 mol) of isocyanatoethyl methacrylate, 1.05 grams of dibutyltin dilaurate and 400 ml. of chloroform was heated under reflux for 4 hours. The solvent was then removed by vacuum stripping and the residue was recrystallized from a mixture of ethyl acetate and hexane. There was obtained 100.5 grams (87% of theoretical) of the desired 3-benzoyloxyphenyl 2-methacryloxyethylcarbamate having a melting point of 57.5°-61.5° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe solvent was then removed by vacuum stripping
  3. customthe residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c2bc31bd2ee64185b254fd29995534bb
Source dataset
uspto-grants-1985_05
Patent number
US04520074

Reaction notes

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