Phthaloyl chloride → Bis[2-(acryloyloxy)ethyl] benzene-1,2-dicarboxylate

HRID 1079285Notes

Reaction equation

HRID 1079285 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5](=[O:8])[CH:6]=[CH2:7].C(N([CH2:14][CH3:15])CC)C.[C:16](Cl)(=[O:26])[C:17]1[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:19](Cl)=[O:20]>CN(C)C1C=CN=CC=1.C1C2NC3C(=CC=CC=3)SC=2C=CC=1.O1CCCC1>[C:5]([O:4][CH2:3][CH2:2][O:1][C:16](=[O:26])[C:17]1[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:19]([O:1][CH2:2][CH2:3][O:4][C:5](=[O:8])[CH:14]=[CH2:15])=[O:20])(=[O:8])[CH:6]=[CH2:7]

Participants

7

Reactant 3

HCID 6955Phthaloyl chlorideHCID 8471TriethylamineHCID 131652-Hydroxyethyl acrylate

Product 1

HCID 54175635Bis[2-(acryloyloxy)ethyl] benzene-1,2-dicarboxylateYield 100.4%

Reagents, catalysts & solvents 3

HCID 7108PhenothiazineCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
17 °C

Procedure

A five liter, three necked flask was equipped with a overhead stirrer, nitrogen atmosphere and addition funnel. The flask was charged with 636 g of 2-hydroxyethylacrylate (5.47 mol.), 547 g of triethylamine (5.41 mol.), 6 g of phenothiazine, 5 g of 4-dimethylaminopyridine and 3000 ml of tetrahydrofuran. The reaction was cooled to 17° C. with a water bath. Next, 563 g of phthaloyl chloride (2.75 mol.) was slowly added over 2.5 hours via the addition funnel. The reaction was stirred an additional 8 hours at room temperature. The triethylamine hydrochloride salt was removed by filtration and the mother liquor evaporated by rotoevaporation to yield an amber colored liquid. The liquid was placed under vacuum (15 mmHg, 2 kPa) and heated to 100° C. for one hour. The resulting liquid was collected to yield 995 g (99%) of the desired product. The product was confirmed by IR and 13C NMR. The preparation of di(acryloyloxyethyl)phthalate from phthalic anhydride and 2-hydroxyethylacrylate was reported in U.S. Pat. No. 3,336,418.

Workup

  1. customA five liter, three necked flask was equipped with a overhead stirrer
  2. additionnitrogen atmosphere and addition funnel
  3. customThe triethylamine hydrochloride salt was removed by filtration
  4. customthe mother liquor evaporated by rotoevaporation
  5. customto yield an amber colored liquid
  6. temperatureheated to 100° C. for one hour
  7. customThe resulting liquid was collected

Sources & evidence

ORD record
ord-2e57eb3a25614bbda3d7913ac36578a0
Source dataset
uspto-grants-1996_12
Patent number
US05580647

Reaction notes

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