Hydrochloric Acid → 4-(4-Oxo-4-phenyl-butyryl)-benzoic acid

HRID 1725158

반응식

HRID 1725158 반응식
C([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:22])[CH2:12][CH2:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)C.[OH-].[K+].Cl>C1COCC1>[O:21]=[C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:13][CH2:12][C:11]([C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:23])=[O:3])=[CH:6][CH:7]=1)=[O:22]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 44520324-(4-Oxo-4-phenyl-butyryl)-benzoic acid ethyl ester

생성물 1

HCID 574236664-(4-Oxo-4-phenyl-butyryl)-benzoic acid수율 99.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

4-(4-Oxo-4-phenyl-butyryl)-benzoic acid ethyl ester (3.22 g, 10.4 mmol) is dissolved in THF (100 mL) and an aqueous solution of KOH (15.6 mmol in 50 mL) is added. The reaction is stirred and heated (65° C.) for 6 h, whereupon HPLC analysis indicated the formation of a single product at the expense of the diketone. The reaction is neutralized with aqueous HCl and the THF removed in vacuo. The resulting solid is dissolved in EtOAc and the organic phase dried (Na2SO4), filtered and concentrated to afford 2.93 g (>99%) of the desired carboxylic acid (RT=0.90). LCMS confirmed the identity of the product (ES+Exact Mass: 282.09, Obs.: 283.48). This product is used without further purification.

후처리

  1. customthe THF removed in vacuo
  2. dissolutionThe resulting solid is dissolved in EtOAc
  3. dry with materialthe organic phase dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1e6484ba8d164384850040eca40f606d
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488832B2

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