2-(2-Hydroxyethyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione → HCID 10896667, compound

HRID 1422265Notes

Reaction equation

HRID 1422265 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[CH:7]2[CH2:10][CH:11]=[CH:12][CH2:13][CH:6]2[C:5]1=[O:14].[C:15]([O:30]CC(C)C)(=O)[CH:16]1[CH2:28][CH:27]=[CH:26][CH2:25][CH:17]1[C:18]([O:20][CH2:21][CH:22](C)C)=[O:19]>[O-]CCCC.[O-]CCCC.[O-]CCCC.[O-]CCCC.[Ti+4].O>[C:18]([O:20][CH2:21][CH2:22][N:4]1[C:5](=[O:14])[CH:6]2[CH2:13][CH:12]=[CH:11][CH2:10][CH:7]2[C:8]1=[O:9])(=[O:19])[CH:17]1[CH2:25][CH:26]=[CH:27][CH2:28][CH:16]1[C:15]([O:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[CH:7]2[CH2:10][CH:11]=[CH:12][CH2:13][CH:6]2[C:5]1=[O:14])=[O:30]

Participants

5

Reactant 2

HCID 858512-(2-Hydroxyethyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dioneHCID 6432739diisobutyl 1,2,3,6-tetrahydrophthalate

Product 1

HCID 10896667HCID 10896667, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 21801Titanium tetrabutoxideCatalystHCID 962WaterSolvent

Conditions

Temperature
230 °C

Procedure

N-(2-Hydroxyethyl)-1,2,3,6-tetrahydrophthalimide (195.2 g, 1 mol) was dissolved in diisobutyl 1,2,3,6-tetrahydrophthalate (141.2 g, 0.5 mol). The mixture was kept at 150° C. under vacuum to eliminate any traces of water. Titanium tetrabutoxide (1.7 g) was added under atmospheric pressure and the transesterification reaction was carried out distilling off the isobutyl alcohol formed. As the reaction proceeded the temperature was increased stepwise to 230° C. and the pressure was lowered to 20 Torr (26.7 mbar). After ca. 24 h, 265 g of brown crude bis[2-(1,2,3,6-tetrahydrophthalimido)ethyl] 1,2,3,6-tetrahydrophthalate were obtained.

Workup

  1. customwas kept at 150° C. under vacuum
  2. customthe transesterification reaction
  3. distillationwas carried out distilling off the isobutyl alcohol
  4. customformed

Sources & evidence

ORD record
ord-2ed3f2956efc461882cb3ca99b5c14d4
Source dataset
uspto-grants-2000_06
Patent number
US06080872

Reaction notes

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