Hydrochloric Acid → 3-Phenylbutyric acid

HRID 593262

反応式

HRID 593262 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]([OH:18])(=[O:17])/[CH:14]=[CH:15]/[CH3:16].Cl>O1CCCC1>[C:7]1([CH:15]([CH3:16])[CH2:14][C:13]([OH:18])=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 637090Crotonic AcidHCID 178418339Butyllithium

生成物 1

HCID 207243-Phenylbutyric acid収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

As presented in the following reaction formula, n-butyllithium (n-BuLi; 428 mL, 1.07 mol) was added dropwise at −78° C. to −65° C. to a mixture of bromobenzene (166 g, 1.07 mol) in tetrahydrofuran (THF; 500 mL), followed by stirring at −78° C. for 0.5 hours. Then, (E)-but-2-enoic acid (46 g, 0.53 mol) was added dropwise to the resulting mixture. After the completion of reaction, the mixture was treated with hydrochloric acid so that the pH thereof was adjusted to 1.0, and then extracted twice with 500 mL of dichloromethane (DCM). The combined organic phase was dried and concentrated with magnesium sulfate to give a crude product, which was purified by column chromatography (using 300 g of silica gel (product of Merck Co., Ltd.) to give 3-phenylbutanoic acid (52 g, yield: 60%) as a yellow liquid.

後処理

  1. customAfter the completion of reaction
  2. extractionextracted twice with 500 mL of dichloromethane (DCM)
  3. customThe combined organic phase was dried
  4. concentrationconcentrated with magnesium sulfate
  5. customto give a crude product, which
  6. customwas purified by column chromatography (

出典と根拠

ORDレコード
ord-d6fb234995ba403ea1a361ffbcd8273f
出典データセット
uspto-grants-2016_01
特許番号
US09242928B2

関連ノート

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