Hydrochloric Acid → 3-Phenylbutyric acid

HRID 593262

반응식

HRID 593262 반응식
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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 637090Crotonic AcidHCID 178418339Butyllithium

생성물 1

HCID 207243-Phenylbutyric acid수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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 (

출처 및 근거

ORD 기록
ord-d6fb234995ba403ea1a361ffbcd8273f
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242928B2

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