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

HRID 1494242ノート

反応式

HRID 1494242 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2c3709ef46e1484ebf26fb811806f030
出典データセット
uspto-grants-1991_06
特許番号
US05025036

反応ノート

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