Acrylic Acid → Acrylic anhydride

HRID 39498ノート

反応式

HRID 39498 の反応式
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]([OH:10])(=[O:9])[CH:7]=[CH2:8].C(N(CC)CC)C>C1COCC1>[C:6]([O:10][C:1](=[O:4])[CH:2]=[CH2:3])(=[O:9])[CH:7]=[CH2:8]

参加物

5

反応物 3

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 13140Acryloyl chloride

生成物 1

HCID 74919Acrylic anhydride収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Acrylic anhydride was synthesized in 70-80% yield as in the following example. Acryloyl chloride (2.7 g, 30 mmol) was added dropwise over 5 min to an ice-cooled solution of acrylic acid (2.0 g, 30 mmol) and triethylamine (2.8 g, 30 mmol) in THF (50 mL), and the solution was stirred at room temperature for 16 h. The NH4+Cl− precipitate was collected in a fritted glass filter, and the solvent was then removed from the filtrate by rotary evaporation. The residue was dissolved in CH2Cl2 (25 mL), washed twice with dilute aq. NaHCO3 (50 mL each) and once with satd. NaCl aq. soln. (50 mL), and dried over anhy. Na2SO4. After filtration and removing the solvent by rotary evaporation, 2.8 g (80%) of acrylic anhydride was obtained as a light yellow liquid. It was used without further purification. 1H NMR (CDCl3, 77.23 ppm): 6.04 (m, ═CH trans to CO2), 6.14 (m, ═CH gem to CO2), 6.50 (d, ═CH cis to CO2). 13C NMR (CDCl3/DMSO-d6): 127.4 (═CH), 134.7 (′CH2), 161.2 (C═O).

後処理

  1. customThe NH4+Cl− precipitate was collected in a fritted glass
  2. filtrationfilter
  3. customthe solvent was then removed from the filtrate by rotary evaporation
  4. dissolutionThe residue was dissolved in CH2Cl2 (25 mL)
  5. washwashed twice with dilute aq. NaHCO3 (50 mL each)
  6. custom(50 mL), and dried over anhy
  7. filtrationAfter filtration
  8. customremoving the solvent
  9. customby rotary evaporation

出典と根拠

ORDレコード
ord-d253399be82a4996b04ae7c34c4661b8
出典データセット
uspto-grants-2013_09
特許番号
US08524942B2

反応ノート

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