Sodium Methoxide → o-Phenylbenzoic acid

HRID 650323ノート

反応式

HRID 650323 の反応式
Cl[C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH:7]=1.Cl[C:20]1[CH2:25][CH2:24][C:23]([C:26]([O:28]CC)=[O:27])=[C:22]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:21]=1.C[O-].[Na+]>CO>[C:13]1([C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][C:5]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.[C:31]1([C:22]2[CH:21]=[CH:20][CH:25]=[CH:24][C:23]=2[C:26]([OH:28])=[O:27])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

参加物

6

反応物 3

HCID 10942334Sodium MethoxideHCID 10967324HCID 10967324、化合物HCID 11043594HCID 11043594、化合物

生成物 2

HCID 70357o-Phenylbenzoic acid収率 53.8%HCID 9920952Ethyl 2-phenylbenzoate収率 23.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of a mixture(620 mg, 2.54 mmol) of ethyl 4-chloro-2-phenylcyclohexa-2,4-dienecarboxylate and ethyl 4-chloro-2-phenylcyclohexa-1,3-dienecarboxylate in MeOH(5 ml), NaOMe(28% in MeOH, 1.98 g, 10.1 mmol) was added. After stirring for 17 hr at room temperature, the solvent was evaporated under reduced pressure. Water was added to the residue and dil. HCl aq., and it was extracted with AcOEt. The organic layer was washed with brine and dried over MgSO4. After removal of the solvent, the residue was purified by column chromatography on silica gel with n-hexane-AcOEt to afford 136 mg of ethyl 2-phenylbenzoate(y=23.7%) and 236 mg of 2-phenylbenzoic acid(y=53.8%). 1H-NMR(ppm, 300 MHz, CDCl3) δ ester 7.82(1H, dd, J=1.4 and 7.7 Hz), 7.10-7.60(8H), 4.08(2H, d, J=7.0 Hz), 0.98(3H, t, J=7.0 Hz); acid 7.95(1H, d, J=7.9 Hz)

後処理

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater was added to the residue and dil. HCl aq., and it
  3. extractionwas extracted with AcOEt
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customAfter removal of the solvent
  7. customthe residue was purified by column chromatography on silica gel with n-hexane-AcOEt

出典と根拠

ORDレコード
ord-f9f8569fcc134b5380064cebe3fa2c8c
出典データセット
uspto-grants-2001_08
特許番号
US06271418B1

反応ノート

読み込み中…