Benzene → HCID 86651356、化合物

HRID 39497

反応式

HRID 39497 の反応式
[Cl:1][CH:2]([CH2:6][OH:7])[C:3]([OH:5])=[O:4].[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[Cl:1][CH:2]([CH2:6][OH:7])[C:3]([O:5][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])=[O:4]

参加物

6

反応物 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 81931-DodecanolHCID 5649512-Chloro-3-hydroxypropionic acid2 回

生成物 1

HCID 86651356HCID 86651356、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-chloro-3-hydroxypropionic acid (4.80 g, 0.03 mol), dodecanol (6.00 g, 0.03 mol) were taken with 5 mL dry benzene in a (50 mL) RB, with a dean-stark apparatus and condenser; 25 mg (0.26 mmol) para-Toluene sulfonic acid (pTSA) was added to it and the mixture was stirred at 75° C.-80° C. for 40 h. 1H-NMR showed 85% conversion. More 2-chloro-3-hydroxypropionic acid (1.00 g, 8.00 mmol) was added to it and heated at 75° C.-80° C. for 20 h. 1H-NMR showed almost complete conversion. After cooling it down, the product was added with 100 mL of CH2Cl2. Organic phase was washed twice with 50 mL of dil. NaHCO3 aq. sol. and once with 50 mL of sat. NaCl aq. sol. and then dried over anhy. Na2SO4. After filtration and removing the solvent by rotary evaporation, yield=7.76 g (78%). It was used for the next reaction without further purification. 1H-NMR (CDCl3, 7.27 ppm): 2.18-2.40 (broad, —OH), 3.97 (m, —CH2OH), 4.21 (m, —CO2CH2), 4.39 (m, —CHCl).

後処理

  1. temperatureheated at 75° C.-80° C. for 20 h
  2. temperatureAfter cooling it down
  3. washOrganic phase was washed twice with 50 mL of dil. NaHCO3 aq. sol. and once with 50 mL of sat. NaCl aq. sol.
  4. customdried over anhy
  5. filtrationAfter filtration
  6. customremoving the solvent
  7. customby rotary evaporation, yield=7.76 g (78%)
  8. customIt was used for the next reaction without further purification

出典と根拠

ORDレコード
ord-dd70758721d642d29d1cf230ba39a7bb
出典データセット
uspto-grants-2013_09
特許番号
US08524942B2

関連ノート

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