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Water → 4-(4-Chlorophenyl)-2-methoxybenzoic acid

HRID 1158569
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HRID 1158569 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:7][C:6]=1[O:18][CH3:19])=[O:4].O.[Li+].[OH-]>C1COCC1>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[C:6]([O:18][CH3:19])[CH:7]=2)=[CH:16][CH:15]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 595130824'-Chloro-3-methoxy-biphenyl-4-carboxylic acid methyl ester

생성물 1

HCID 248911994-(4-Chlorophenyl)-2-methoxybenzoic acid수율 91%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4′-chloro-3-methoxy-biphenyl-4-carboxylic acid methyl ester, 8, (0.615 g, 2.22 mmol) in THF (20 mL) and H2O (5 mL) at room temperature is added LiOH (0.932 g, 22.2 mmol). The resulting suspension is heated to reflux for 2 hours. The reaction is cooled and concentrated under reduced pressure. The crude product is acidified using conc. HCl and the resulting solid is collected by filtration washed with H2O and dried to afford 0.532 g (91%) of the desired product as a grey solid. 1H NMR (400 MHz, CDCl3) δ ppm 10.69 (1H, br s), 8.26 (1H, d, J=8.1 Hz), 7.53-7.58 (2H, m), 7.44-7.50 (2H, m), 7.33 (1H, dd, J=8.1, 1.6 Hz), 7.20 (1H, d, J=1.3 Hz), 4.17 (3H, s). HPLC-MS: m/z 263 [M+H]+.

후처리

  1. temperatureThe resulting suspension is heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction is cooled
  4. concentrationconcentrated under reduced pressure
  5. filtrationthe resulting solid is collected by filtration
  6. washwashed with H2O
  7. customdried

출처 및 근거

ORD 기록
ord-a71312a5fd6b4db58b6c20e3e5d11696
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07811595B2

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