Styrene → Dimethyl 2-phenyl-cyclohexane-1,4-dicarboxylate

HRID 385202

反応式

HRID 385202 の反応式
[C:1]([O:11][CH3:12])(=[O:10])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[C:6]([O:8][CH3:9])=[O:7].[CH2:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(C1C=CC=C(O)C=1O)(C)(C)C>COCCOCCOC>[C:15]1([CH:14]2[CH2:13][CH:2]([C:1]([O:11][CH3:12])=[O:10])[CH2:3][CH2:4][CH:5]2[C:6]([O:8][CH3:9])=[O:7])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 7501StyreneHCID 77643tert-ButylcatecholHCID 5370244Dimethyl muconate, (E,E)-

生成物 1

HCID 66809627Dimethyl 2-phenyl-cyclohexane-1,4-dicarboxylate

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

反応条件

温度
150 °C

実験手順

In a 75 ml sealed tube, a stirred suspension of trans,trans dimethyl muconate (10.0 g, 58.8 mmol), two equivalents of styrene (13.5 ml, 117.6 mmol), neutral Al2O3 (300 mg of Aldrich 199974, 3 mass percent), and tert-butyl catechol (25 mg, 0.2 mol percent) in diglyme (20 ml, 2.9 M) is heated to 150° C. for 24 hours. After cooling to room temperature, the reaction mixture is filtered, transferred to a flask, and concentrated. The residue is redissolved in triglyme (0.5 M). Pd/Al2O3 catalyst is added (636 mg (0.5 mol percent) of Johnson-Matthey 5 percent Pd/Al2O3 #12) at room temperature. The flask is equipped with a reflux condenser, fritted gas dispersion tube, and internal Temperature probe. Under N2 flow (190 ml/min) and stirring (190 rpm) the mixture is heated to reflux for 63 hours whereby dimethyl phenyl-terephthalate is formed. Some dimethyl 2-phenyl-cyclohexane-1,4-dicarboxylate is also produced.

後処理

  1. customIn a 75 ml sealed tube
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture is filtered
  4. customtransferred to a flask
  5. concentrationconcentrated
  6. dissolutionThe residue is redissolved in triglyme (0.5 M)
  7. additionPd/Al2O3 catalyst is added (636 mg (0.5 mol percent) of Johnson-Matthey 5 percent Pd/Al2O3 #12) at room temperature
  8. customThe flask is equipped with a reflux condenser, fritted gas dispersion tube
  9. temperatureis heated
  10. temperatureto reflux for 63 hours whereby dimethyl phenyl-terephthalate
  11. customis formed

出典と根拠

ORDレコード
ord-a4e90c49928f47ad8a5c1945dff64f0a
出典データセット
uspto-grants-2013_02
特許番号
US08367858B2

関連ノート

読み込み中…