Dimethylformamide → Methyl 4'-methoxy(1,1'-biphenyl)-4-carboxylate

HRID 493503

반응식

HRID 493503 반응식
[CH2:1](N(CC)CC)C.O[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].IC.CN([CH:35]=[O:36])C>C(Cl)Cl>[CH3:1][O:23][C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:36][CH3:35])=[CH:10][CH:11]=2)=[CH:16][CH:17]=1)=[O:22]

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

생성물 1

HCID 1393415Methyl 4'-methoxy(1,1'-biphenyl)-4-carboxylate수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (9.76 mL, 70 mmol) was added under nitrogen to a solution of 4′-hydroxy-biphenyl-4-carboxylic acid (15.0 g, 70 mmol) in 200 mL of anhydrous DMF at room temperature. After stirring for 5 minutes potassium carbonate (58.0 g, 420 mmol) was added and the reaction stirred an additional 5 minutes. Iodomethane (26.0 mL, 420 mmol) was then added (exothermic reaction) and the reaction stirred overnight. The reaction was diluted with methylene chloride, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 4′-methoxy-biphenyl-4-carboxylic acid methyl ester (16.26 g, 96%) as a tan solid, mp 170-173° C. Elemental Analysis for C15H14O3: Calc'd: C, 74.36; H, 5.82; N, 0.00; Found: C, 73.97; H, 5.66; N, 0.03.

후처리

  1. additionwas added
  2. custom(exothermic reaction)
  3. stirringthe reaction stirred overnight
  4. extractionextracted multiple times with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-7593faf78e8b464daa4635e444d5e85d
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534894B2

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