Triethylamine → 2-[4-(4-Phenoxyphenoxy)phenyl)ethyl acrylate

HRID 926821Notes

Reaction equation

HRID 926821 reaction equation
[O:1]([C:8]1[CH:23]=[CH:22][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:34])[CH:32]=[CH2:33]>C(Cl)Cl>[C:31]([O:21][CH2:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:11]2[CH:22]=[CH:23][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:9][CH:10]=2)=[CH:14][CH:15]=1)(=[O:34])[CH:32]=[CH2:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 1181079682-(4-(4-Phenoxyphenoxy)phenyl]ethanol

Product 1

HCID 1181079642-[4-(4-Phenoxyphenoxy)phenyl)ethyl acrylateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 1 L three-neck round bottom flask equipped with mechanical stirrer were charged 2-[4-(4-phenoxyphenoxy)phenyl]ethanol (61.2 g, 0.2 mol), anhydrous triethylamine (60 mL, 0.42 mol), and anhydrous methylene chloride (300 mL). The solution was cooled in an ice/salt bath under dry air blanket for 15 mins. Acryloyl chloride (22 mL, 0.27 mol) was added into the vigorously stirred cold solution through an addition funnel over 60 min and the addition rate was adjusted to keep the temperature of the reaction mixture below 10° C. After the addition, the reaction mixture was stirred in the ice/salt bath for additional two hours followed by quenching with the addition of 2M HCl (300 mL). The mixture was extracted with ethyl acetate (300 mL×3) and the combined organic layer was washed with DI water (200 mL×3), aqueous sodium bicarbonate (200 mL×2), and dried over MgSO4. Filtration and removal of solvents under reduced pressure gave the crude product as light brown oil which was purified on silica gel using Hexanes/Ethyl acetate (9/1, v/v) as eluent to give P3E2EA as a white powder (62 g, 86%).

Workup

  1. customTo a 1 L three-neck round bottom flask equipped with mechanical stirrer
  2. temperatureThe solution was cooled in an ice/salt bath
  3. customunder dry air blanket for 15 mins
  4. customthe temperature of the reaction mixture below 10° C
  5. additionAfter the addition
  6. customby quenching with the addition of 2M HCl (300 mL)
  7. extractionThe mixture was extracted with ethyl acetate (300 mL×3)
  8. washthe combined organic layer was washed with DI water (200 mL×3), aqueous sodium bicarbonate (200 mL×2)
  9. dry with materialdried over MgSO4
  10. filtrationFiltration and removal of solvents under reduced pressure
  11. customgave the crude product as light brown oil which
  12. customwas purified on silica gel

Sources & evidence

ORD record
ord-b72c8b669f6f457c851c7bc878e12502
Source dataset
uspto-grants-2016_03
Patent number
US09289531B2

Reaction notes

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