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

HRID 2075924

反応式

HRID 2075924 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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 1 M 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).

後処理

  1. customreaction mixture overnight at rt
  2. customQuench
  3. customreaction mixture (cooling bath) with 1 M 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

出典と根拠

ORDレコード
ord-670cf59593f24961a470183b963a1973
出典データセット
uspto-grants-2011_04
特許番号
US07923473B2

関連ノート

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