Thioglycolic Acid → 6-Hydroxy-7-methoxyphthalide

HRID 1656544Notes

Reaction equation

HRID 1656544 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:8](O)(=[O:11])CS.CC(N=NC(C#N)(C)C)(C#N)C.[C:25](OCC1OC1)(=[O:29])[C:26](C)=[CH2:27].CN(CCCCCCCCCCCC)C.C(C1C=C(O)C=CC=1O)(C)(C)C>C1(C)C=CC=CC=1>[CH3:8][O:11][C:4]1[C:2]2[C:1]([O:6][CH2:7][C:3]=2[CH:27]=[CH:26][C:25]=1[OH:29])=[O:5]

Participants

8

Reactant 6

HCID 1133Thioglycolic AcidHCID 6547AzobisisobutyronitrileHCID 6658Methyl MethacrylateHCID 7837Glycidyl methacrylateHCID 8168LauryldimethylamineHCID 16043Tert-Butylhydroquinone

Product 1

HCID 1960756-Hydroxy-7-methoxyphthalide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixed solution of 95 g of methyl methacrylate, 5 g of thioglycolic acid, and 200 g of toluene was heated to 70° C. with stirring under nitrogen gas stream. To the mixture was added 1.5 g of AIBN to conduct a reaction for 8 hours. To the reaction mixture were added 7.5 g of glycidyl methacrylate, 1.0 g of N,N-dimethyldodecylamine, and 0.8 g of tert-butylhydroquinone, followed by stirring at 100° C. for 12 hours. After cooling, the reaction mixture was reprecipitated from 2 l of methanol to obtain 85 g of Macromonomer (MA-2) having an Mw of 4.5×103 as a colorless clear viscous substance.

Workup

  1. customa reaction for 8 hours
  2. stirringby stirring at 100° C. for 12 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was reprecipitated from 2 l of methanol

Sources & evidence

ORD record
ord-8ac39f0a013c4a7ba7eec32c5b2cb0a5
Source dataset
uspto-grants-1993_10
Patent number
US05254422

Reaction notes

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