Oxygen → 2-Methyl-5-methyleneadipic acid

HRID 1425618

反応式

HRID 1425618 の反応式
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:7][C:8](=[CH2:17])[C:9]([O:11]C(=O)C(C)=C)=[O:10].O=O>>[CH3:3][CH:2]([CH2:4][CH2:17][C:8](=[CH2:7])[C:9]([OH:11])=[O:10])[C:1]([OH:6])=[O:5]

参加物

4

反応物 3

HCID 977OxygenHCID 4093Methacrylic AcidHCID 12974Methacrylic anhydride

生成物 1

HCID 1106472-Methyl-5-methyleneadipic acid収率 97%

反応条件

温度
120 °C

実験手順

To a mechanically stirred solution of 2 moles of hydroxyquinone dissolved in 3 moles of methacrylic acid at 120° C. and atmospheric pressure was added dropwise (30 min) 1 mole of methylacrylic acid anhydride and the mixture was maintained at 120° C. with stirring for additional 4 hrs (NMR analysis). Throughout the course of the reaction 8% oxygen was admitted to the system. At the end of the reaction, the methacrylic acid was recovered by distillation under reduced pressure (110° C. and 200 mmHg), and the unreacted excess hydroquinone was precipitated out by the addition of toluene (1 liter) to the reaction mixture. A low level (1-2%) of the monomer 2-methyl-5-methylenehexanedioic acid was formed. This monomer was separated from the mixture by a washing step with distilled water. After phase separation, the desired 4-hydroxyphenyl methacrylate was obtained at 97% yield by the distillation of toluene under reduced pressure. {mp. (Uncorrected) 120° C.; Anal. Calcd. For C10H10O3: C, 67.41: H, 5.66; O, 26.94. Found: C, 67.37; H, 5.62}.

後処理

  1. customAt the end of the reaction
  2. distillationthe methacrylic acid was recovered by distillation under reduced pressure (110° C. and 200 mmHg)
  3. customthe unreacted excess hydroquinone was precipitated out by the addition of toluene (1 liter) to the reaction mixture

出典と根拠

ORDレコード
ord-b0372d4cad9c410492ceedddfdb384d7
出典データセット
uspto-grants-2015_01
特許番号
US08932793B2

関連ノート

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