Hydrochloric Acid → 2',3',4'-Trimethoxy-biphenyl-3-carboxylic acid

HRID 1944253

반응식

HRID 1944253 반응식
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[C:12]=2[O:21][CH3:22])[CH:8]=[CH:9][CH:10]=1)=[O:4].[Li+].[OH-].Cl>CC#N>[CH3:22][O:21][C:12]1[C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]=1[C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 161162902',3',4'-Trimethoxy-biphenyl-3-carboxylic acid methyl ester

생성물 1

HCID 160407182',3',4'-Trimethoxy-biphenyl-3-carboxylic acid수율 72.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Dissolve 2′,3′,4′-Trimethoxy-biphenyl-3-carboxylic acid methyl ester (33) (566 mg, 1.87 mmol) in MeCN (19.0 mL) at rt and add 1M aqu LiOH (9.36 mL, 9.36 mmol). Stir reaction mixture overnight at rt. Quench reaction mixture (cooling bath) with 1M aqu. HCl (to get pH ca. 3). Extract the mixture with EtOAc (3×), wash the combined organic layer with brine and dry with Na2SO4. Recrystallize crude product from EtOAc/CyH 1+3 to obtain 2′,3′,4′-Trimethoxy-biphenyl-3-carboxylic acid (34) as a white solid (392 mg, 72%). 1H NMR (400 MHz, CD3OD: 3.68 (s, 3H); 3.93 (br.s, 6H); 6.92 (d, 1H, J=8.6 Hz); 7.11 (d, 1H, J=8.6 Hz); 7.54 (t, 1H, J=7.7 Hz); 7.75 (d, 1H, J=7.6 Hz); 8.01 (d, 1H, J=7.8 Hz); 8.18 (br.s 1H).

후처리

  1. customreaction mixture overnight at rt
  2. customQuench
  3. customreaction mixture (cooling bath) with 1M aqu
  4. extractionExtract the mixture with EtOAc (3×)
  5. washwash the combined organic layer with brine
  6. dry with materialdry with Na2SO4
  7. customRecrystallize crude product from EtOAc/CyH 1+3

출처 및 근거

ORD 기록
ord-4ae068c4617b42bbbd93d0c00c7d862a
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394835B2

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