Potassium Iodide → 4-[3-(3,4-Dimethoxyphenyl)propoxy]-2-hydroxy-3-propylbenzoic acid methyl ester

HRID 1494242노트

반응식

HRID 1494242 반응식
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[CH3:15][O:16][C:17](=[O:29])[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:25][CH2:26][CH3:27])[C:19]=1[OH:28].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:15][O:16][C:17](=[O:29])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:2][CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=2)=[C:20]([CH2:25][CH2:26][CH3:27])[C:19]=1[OH:28]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 127653884-(3-Bromopropyl)-1,2-dimethoxybenzeneHCID 13019281Methyl 2,4-dihydroxy-3-propylbenzoate

생성물 1

HCID 149863534-[3-(3,4-Dimethoxyphenyl)propoxy]-2-hydroxy-3-propylbenzoic acid methyl ester수율 56.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of 9.5 g (0.037 mol) of 1-(3-bromopropyl)-3,4-dimethoxybenzene [G. H. Douglas, C. R. Walk and H. Smith, J. Med. Chem., 9, 27 (1966)], 7.0 g (0.033 mol) of 2,4-dihydroxy-3-propylbenzoic acid methyl ester, 6.9 g (0.05 mol) of potassium carbonate and 8.3 g (0.05 mol) of potassium iodide in 250 mL of acetone was stirred at reflux for 24 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to an oil which was purified by high pressure liquid chromatography using 15% ethyl acetate-hexane to give 7.2 g (56% yield) of 4-[3-(3,4-dimethoxyphenyl)propoxy]-2-hydroxy-3-propylbenzoic acid methyl ester as an oil.

후처리

  1. temperatureat reflux for 24 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure to an oil which
  4. customwas purified by high pressure liquid chromatography

출처 및 근거

ORD 기록
ord-2c3709ef46e1484ebf26fb811806f030
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05025036

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