Hydroquinone → 5-Norbornen-2-ylmethyl methacrylate

HRID 972909

反応式

HRID 972909 の反応式
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][OH:9].[C:10](OC)(=[O:14])[C:11]([CH3:13])=[CH2:12].C1(C=CC(O)=CC=1)O.C[O-].[Na+]>CN(C)C=O.O>[C:10]([O:9][CH2:8][CH:2]1[CH2:3][CH:4]2[CH2:7][CH:1]1[CH:6]=[CH:5]2)(=[O:14])[C:11]([CH3:13])=[CH2:12]

参加物

7

反応物 4

HCID 785HydroquinoneHCID 6658Methyl MethacrylateHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanolHCID 10942334Sodium Methoxide

生成物 1

HCID 148327955-Norbornen-2-ylmethyl methacrylate

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

5-norbornen-2-ylmethyl methacrylate monomer was prepared in a flask fitted with a vertical condenser with water at 75° C circulating through the jacket, attached at the top to a downwards cold water-cooled condenser. There were refluxed for 2 hours 372 grams (3.0 moles) of 5-norbornen -2-methanol, 450 grams (4.5 moles) of methyl methacrylate, 526 grams of N,N-dimethylformamide, 28.8 grams of hydroquinone, and 8.1 grams (0.15 mole) of sodium methoxide. A total of 252 ml of distillate was collected (theoretical methanol equals 121 ml.). The flask contents were cooled, diluted with ether, and washed with water, excess dilute hydrochloric acid, water, 5% aqueous sodium hydroxide until the washes were colorless, and again with water. The ether solution was dried with anhydrous sodium sulfate, 11.5 grams of p-(p-tolylsulfonyl-amido) diphenylamine were added, and the ether was removed in a rotary evaporator at 60° C and about 15 mm pressure. To the residual oil 0.58 gram of hydroquinone was added and the product was distilled through a Vigreux column to give 431 grams of product having a boiling point of 770 C/1.4 mm, nD20 = 1.4848. The monomer was then passed through a column of activated sodium aluminum silicate.

後処理

  1. temperaturecooled condenser
  2. distillationA total of 252 ml of distillate was collected (theoretical methanol equals 121 ml.)
  3. temperatureThe flask contents were cooled
  4. additiondiluted with ether
  5. washwashed with water, excess dilute hydrochloric acid, water, 5% aqueous sodium hydroxide until the washes
  6. dry with materialThe ether solution was dried with anhydrous sodium sulfate, 11.5 grams of p-(p-tolylsulfonyl-amido) diphenylamine
  7. additionwere added
  8. customthe ether was removed in a rotary evaporator at 60° C
  9. additionTo the residual oil 0.58 gram of hydroquinone was added
  10. distillationthe product was distilled through a Vigreux column

出典と根拠

ORDレコード
ord-0b363bdc88d2441baade74e307407233
出典データセット
uspto-grants-1977_10
特許番号
US04054233

関連ノート

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