Triethylamine → 9-Anthracenylmethyl acrylate

HRID 1648793Notes

Reaction equation

HRID 1648793 reaction equation
[OH:1][CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.C(N(CC)CC)C.C(C1[C:33]([OH:34])=[C:32](C(C)(C)C)[CH:31]=C(C)C=1)(C)(C)C.C(Cl)(=O)C=C>O.C(OCC)C>[C:33]([O:1][CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2)(=[O:34])[CH:32]=[CH2:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 738489-Anthracenemethanol

Product 1

HCID 40652319-Anthracenylmethyl acrylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 9-hydroxymethylanthracene (20.8 g, 0.1 mol) and triethylamine (11.1 g, 0.11 mol), containing 0.05 g of 2,6-di-tert.butyl-p-cresol, in 200 ml of freshly distilled diethyl ether was cooled with stirring to 0° C., and the temperature of the mixture was kept at about this level while acryloyl chloride (9.32 g, 0.103 mol) was added. The mixture was then warmed to refluxing temperature and heated to reflux for 2 hours. After the mixture had been cooled, 200 ml. of water was added, and the two layers were separated. The organic layer was washed twice with 50 ml portions of cold 10% sulphuric acid and then with a saturated aqueous solution of sodium bicarbonate, while the aqueous acid layer was extracted further with dichloromethane, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate. Finally, the two organic solutions were mixed, dried over anhydrous magnesium sulphate, and the solvents distilled off. There remained 11.1 g of the title compound as a yellow, semicrystalline oil. It solidified on standing and then had m.pt. 120°-125° C.

Workup

  1. additionwas added
  2. temperatureThe mixture was then warmed
  3. temperatureto refluxing temperature
  4. temperatureheated
  5. temperatureto reflux for 2 hours
  6. temperatureAfter the mixture had been cooled
  7. customthe two layers were separated
  8. washThe organic layer was washed twice with 50 ml portions of cold 10% sulphuric acid
  9. extractionwith a saturated aqueous solution of sodium bicarbonate, while the aqueous acid layer was extracted further with dichloromethane
  10. washthe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  11. additionFinally, the two organic solutions were mixed
  12. dry with materialdried over anhydrous magnesium sulphate
  13. distillationthe solvents distilled off

Sources & evidence

ORD record
ord-56fbcc101ce0449480c197c92a95045c
Source dataset
uspto-grants-1983_11
Patent number
US04413052

Reaction notes

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