2,2'-(p-Phenylenedioxy)diethanol → HCID 54127676、化合物

HRID 1741804ノート

反応式

HRID 1741804 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([Cl:11])[CH:5]=1.[CH:13]1[C:18]([O:19][CH2:20][CH2:21][OH:22])=[CH:17][CH:16]=[C:15]([O:23][CH2:24]CO)[CH:14]=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:22][CH2:21][CH2:20][O:19][C:18]1[CH:13]=[CH:14][C:15]([O:23][CH2:24][CH2:1][O:2][C:3](=[O:12])[C:4]2[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([Cl:11])[CH:5]=2)=[CH:16][CH:17]=1

参加物

4

反応物 2

HCID 669122,2'-(p-Phenylenedioxy)diethanolHCID 77580Methyl 3-chloro-4-hydroxybenzoate

生成物 1

HCID 54127676HCID 54127676、化合物収率 94.1%

試薬・触媒・溶媒 1

HCID 521998p-Toluenesulfonic acid monohydrate触媒

実験手順

A 300-ml eggplant type flask was charged with 16.3 g of 3-chloro-4-hydroxybenzoic acid methyl ester, 87 g of 1,4-(2-hydroxyethoxy)benzene and further with 0.8 g of PTD (p-toluenesulfonic acid monohydrate) as a catalyst to form a mixture. The mixture was stirred with heating on an oil bath, externally regulated at a temperature of 150° C., to react the mixture for 5 hours. The reaction mixture was poured into ice water followed by extracting with ethyl acetate, drying over anhydrous magnesium sulfate, concentrating and separating with a column using ethylacetate/n-hexane to obtain 29 g of 3-chloro-4-hydroxybenzoic acid 2-[4-(β-hydroxyethoxy)-phenoxy]ethyl ester (melting point: 87° to 88° C.). To 50 ml of an acetonitrile solution containing 10 g of the 3-chloro-4-hydroxybenzoic acid 2-[4-(β-hydroxyethoxy)-phenoxy]ethyl ester, 13.9 g of N-methylpyrrolidone and further 8.78 g of methacrylic acid chloride were added with stirring to form a solution. The solution was stirred at 40° C. for 8 hours to react the solution. Thereafter, excess methacrylic acid chloride was removed by means of vacuum distillation. The reaction mixture remaining therein was poured into ice water and the precipitated crystals were obtained by filtration. The crystals were recrystallized with ethylacetate/n-hexane to obtain 3-chloro-4-hydroxybenzoic acid 2-[4-(β-methacryloyloxyethoxy)phenoxy]ethyl ester (melting point: 105° to 106° C.).

後処理

  1. customto form a mixture
  2. temperaturewith heating on an oil bath
  3. customexternally regulated at a temperature of 150° C.
  4. customto react the mixture for 5 hours
  5. extractionby extracting with ethyl acetate
  6. dry with materialdrying over anhydrous magnesium sulfate
  7. concentrationconcentrating
  8. customseparating with a column

出典と根拠

ORDレコード
ord-9e321652353c445f8b2a6db4313b3d61
出典データセット
uspto-grants-1994_08
特許番号
US05334749

反応ノート

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