Methyl iodide → P-tert-Butoxy-alpha-methyl styrene

HRID 746197

反応式

HRID 746197 の反応式
[Mg].Cl[C:3]1[CH:11]=[CH:10][C:6]([C:7]([CH3:9])=[CH2:8])=[CH:5][CH:4]=1.CI.[C:14]([O:18]OC(=O)C1C=CC=CC=1)([CH3:17])([CH3:16])[CH3:15].C(C1C=CC(C2C=CC(C(C)=C)=CC=2)=CC=1)(C)=C>C(OCC)C.O1CCCC1>[C:14]([O:18][C:3]1[CH:11]=[CH:10][C:6]([C:7]([CH3:9])=[CH2:8])=[CH:5][CH:4]=1)([CH3:17])([CH3:16])[CH3:15]

参加物

8

反応物 5

HCID 6328Methyl iodideHCID 11966tert-Butyl peroxybenzoateHCID 743814-Chloro-alpha-methylstyreneHCID 5462224MagnesiumHCID 134223734,4'-Diisopropenylbiphenyl

生成物 1

HCID 11206291P-tert-Butoxy-alpha-methyl styrene収率 69.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

The procedure of Example 1 was repeated, except that there was utilized 16.9 grams (0.70 mole) of magnesium metal and 100 grams (0.66 mole) of 4-chloro-α-methylstyrene dissolved in 200 ml. of tetrahydrofuran. The Grignard reaction was started by the addition of a small amount of methyl iodide. After the reaction mixture had been refluxed for 12 hours, there was added at 0° C. in a dropwise manner a solution of 85 grams of t-butylperbenzoate in 300 ml. of ethylether. A crystalline product identified as 4,4'-diisopropenylbiphenyl was isolated from the oil which was recovered by filtering the mixture and washing with methanol. After stripping the methanol, a 69.3% yield of 4-t-butoxy-α-methylstyrene was isolated by fractional distillation as a colorless liquid having a boiling point of 65°-68° C. at 0.03 millimeters.

後処理

  1. dissolutiondissolved in 200 ml
  2. customThe Grignard reaction
  3. temperatureAfter the reaction mixture had been refluxed for 12 hours
  4. customwas isolated from the oil which
  5. customwas recovered
  6. filtrationby filtering the mixture
  7. washwashing with methanol

出典と根拠

ORDレコード
ord-63997216ebee447ba405a25cc1993547
出典データセット
uspto-grants-1986_07
特許番号
US04603101

関連ノート

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