Water → 2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

HRID 400742노트

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HRID 400742 반응식
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([O:12]C)=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].[OH-].[Na+].O>CCO>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 58554139Methyl 2-(methoxymethyl)-2'-methyl-[1,1'-biphenyl]-4-carboxylate

생성물 1

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid수율 92.6%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

To a solution of methyl 2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylate obtained in step 3 (40 g; 147.97 mmol) in EtOH (1200 mL) was added NaOH (88.78 mL; 5 M; 443.90 mmol) after which the mixture was heated at 60° C. for one hour. Reaction mixture was cooled to room temperature and concentrated under vacuum to give a yellow solid. Water was added and the aqueous phase was washed with EtOAc. The aqueous phase was then acidified with HCl (1 M) and extracted with EtOAc to give the title compound as a yellow solid (35.1 g, 92%). 1H NMR (DMSO-d6) δ 12.99 (br s, 1H), 8.09 (s, 1H), 7.92-7.89 (m, 1H), 7.33-7.22 (m, 4H), 7.10-7.08 (m, 1H), 4.11 (m, 2H), 3.18 (s, 3H), 1.99 (s, 3H). HPLC (Method A) Rt 4.52 min (Purity: 96.4%). LC/MS (Method B): 255.2 (M−H)−.

후처리

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. concentrationconcentrated under vacuum
  4. customto give a yellow solid
  5. washthe aqueous phase was washed with EtOAc
  6. extractionextracted with EtOAc

출처 및 근거

ORD 기록
ord-6395ceaf6725416c83ae6143f3a7a53d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741923B2

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