Trichloroacetyl chloride → HCID 15531479、化合物

HRID 1170425ノート

反応式

HRID 1170425 の反応式
[CH2:1]([O:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]=[CH2:3].[Cl:13][C:14]([Cl:19])(Cl)[C:15](Cl)=[O:16].C(COC)OC.CCCCCC>C(OCC)C.[Zn]>[C:5]([O:4][CH2:1][CH:2]1[CH2:3][C:15](=[O:16])[C:14]1([Cl:19])[Cl:13])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

7

反応物 4

HCID 6420Trichloroacetyl chlorideHCID 8058HexaneHCID 80711,2-DimethoxyethaneHCID 11406Allyl benzoate

生成物 1

HCID 15531479HCID 15531479、化合物収率 37.1%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒2 回HCID 3283Diethyl Ether溶媒2 回

実験手順

To a suspension of benzoic acid allyl ester (100 g, 0.617 mol) and zinc (activated Zn) (161 g, 2.47 mol) in diethyl ether (1.23 L) was added dropwise a solution of trichloroacetyl chloride (223 g, 1.23 mol) and dimethoxyethane (110 g, 1.23 mol) in diethyl ether (1.23 L, 2 L/mol) over 40 minutes under nitrogen with vigorously stirring, and then the mixture was stirred at room temperature (internal temperature: 30° C.) for 29 hours. During the stirring, additional zinc (activated Zn) (respectively, 150 g (2.29 mol) and 100 g (1.53 mol)) was added at 7 and 24 hours after the beginning of the stirring. To the reaction mixture was added hexane (1 L), and the mixture was stirred for 10 minutes, and then the solid was removed by decantation and the supernatant was washed with water (1 L), aqueous saturated sodium bicarbonate solution (3×1 L) and saturated saline (500 mL), and dried over magnesium sulfate. The mixture was evaporated and the precipitated white solid was collected by filtration and washed with hexane (500 mL) to give the titled compound (62.5 g, 37%).

後処理

  1. stirringthe mixture was stirred at room temperature (internal temperature: 30° C.) for 29 hours
  2. stirringthe mixture was stirred for 10 minutes
  3. customthe solid was removed by decantation
  4. washthe supernatant was washed with water (1 L), aqueous saturated sodium bicarbonate solution (3×1 L) and saturated saline (500 mL)
  5. dry with materialdried over magnesium sulfate
  6. customThe mixture was evaporated
  7. filtrationthe precipitated white solid was collected by filtration
  8. washwashed with hexane (500 mL)

出典と根拠

ORDレコード
ord-648d01c7fd864f168256fe4cd03a7535
出典データセット
uspto-grants-2010_11
特許番号
US07825155B2

反応ノート

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