Sodium Hydroxide → 2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

HRID 572544노트

반응식

HRID 572544 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+]>CCO.O>[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 2

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

생성물 1

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid수율 92.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A solution of methyl 2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylate (40 g; 148 mmol; 1 eq.) in EtOH (1.2 L) at RT was treated with NaOH (89 mL; 5 M; 445 mmol). The reaction mixture was stirred at 60° C. for 1 hour. The reaction mixture was cooled to RT and concentrated to give a yellow solid which was taken up in water (800 mL) and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with HCl cc (40 mL) to pH 2 and it was extracted with EtOAc (2×400 mL). The combined organics were washed with brine, dried over MgSO4 and concentrated affording the title compound as a yellow solid (35 g, 92%). 1H NMR (DMSO-d6, 300 MHz) 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). LC/MS (Method B): 255.2 (M−H)−. HPLC (Method A) Rt 4.52 min (Purity: 96.4%).

후처리

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated
  3. customto give a yellow solid which
  4. washthe aqueous phase was washed twice with EtOAc
  5. extractionwas extracted with EtOAc (2×400 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-329cd78f5c6743b6a0bd669dff1c1fb9
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029405B2

반응 노트

불러오는 중…