Phenylacetic Acid → 1-(2-Hydroxy-5-methoxyphenyl)-2-phenylethanone

HRID 239613

反応式

HRID 239613 の反応式
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl.CN(C=O)C>[OH:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][C:21]=1[C:8](=[O:10])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 999Phenylacetic AcidHCID 90161,4-DimethoxybenzeneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 27756071-(2-Hydroxy-5-methoxyphenyl)-2-phenylethanone収率 49%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Phenylacetic acid (7.39 g, 54.28 mmoles) was dissolved in 50 ml dichloromethane. To this mixture, oxalylchloride (4.74 ml, 54.28 mmoles) and DMF (3 drops) were added at 0° C. and stirred for 30 min. The solvent was evaporated and dissolved in 30 ml dichloromethane. To this mixture, 4-methoxyanisole (10 g, 53.47 mmoles) was added and cooled to 0° C. At 0° C. AlCl3 (9.63 g, 72.37 mmoles) was added and the reaction mixture was warmed to RT and stirred for 12 h. The reaction mixture was quenched by the addition of 2N HCl and extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as yellow liquid (4.3 g, 49% yield. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 11.30(s,1H), 7.42(d, J=3.0 Hz, 1H), 7.33-7.21(m, 5H), 7.17(dd, J=9.0,3.1 Hz, 1H), 6.92(d, J=9.0 Hz, 1H), 4.43(s, 2H), 3.74(s, 3H).

後処理

  1. customThe solvent was evaporated
  2. dissolutiondissolved in 30 ml dichloromethane
  3. customAt 0° C
  4. temperaturethe reaction mixture was warmed to RT
  5. stirringstirred for 12 h
  6. customThe reaction mixture was quenched by the addition of 2N HCl
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography with ethyl acetate

出典と根拠

ORDレコード
ord-1ff2464d4bd845e6bd105a1a379db1b0
出典データセット
uspto-grants-2014_02
特許番号
US08642607B2

関連ノート

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