Dimethyl Disulfide → 3-Methylthio-4-hydroxy-5-benzyloxybenzaldehyde

HRID 1085810ノート

反応式

HRID 1085810 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]=1[OH:10])[CH:5]=[O:6].[CH3:19][S:20]SC>N1C=CC=CC=1>[CH3:19][S:20][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]=1[OH:10])[CH:5]=[O:6]

参加物

4

反応物 2

HCID 12232Dimethyl DisulfideHCID 150782813-Bromo-4-hydroxy-5-benzyloxybenzaldehyde

生成物 1

HCID 117781083-Methylthio-4-hydroxy-5-benzyloxybenzaldehyde

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
90 °C

実験手順

A five liter flask equipped with a mechanical stirrer was charged with 100 g of 3-bromo-4-hydroxy-5-benzyloxybenzaldehyde, 80 g Cu powder, 80 mL methyldisulfide and 1.7L pyridine, and the mixture was heated at 90° C. overnight with gentle stirring. The following day, the reaction mixture was filtered and most of the pyridine (1.3L) was distilled off. The remaining solid residue was washed with about 2L of methylene chloride and combined with the residue left after pyridine evaporation. The combined organic fraction was washed with 1.5N HCI until the dark methylene chloride layer turned light brown and the aqueous layer was clear. The resulting light brown methylene chloride layer was dried over MgSO4 and filtered through a bed of silica gel. Evaporation and crystallization from methylene chloride-hexane gave the title compound: NMR(200 MHz, CDCl3) δ 2.50(s, SCH3), 5.20(s, OCH2Ar), 6.72(s, OH), 7.34-7.46(m, ArH), 9.78(s, ArCHO).

後処理

  1. customA five liter flask equipped with a mechanical stirrer
  2. filtrationThe following day, the reaction mixture was filtered and most of the pyridine (1.3L)
  3. distillationwas distilled off
  4. washThe remaining solid residue was washed with about 2L of methylene chloride
  5. waitleft
  6. customafter pyridine evaporation
  7. washThe combined organic fraction was washed with 1.5N HCI until the dark methylene chloride layer
  8. dry with materialThe resulting light brown methylene chloride layer was dried over MgSO4
  9. filtrationfiltered through a bed of silica gel
  10. customEvaporation and crystallization from methylene chloride-hexane

出典と根拠

ORDレコード
ord-e0e528b8a8b3404bb0c37ffd7a606e4b
出典データセット
uspto-grants-1991_04
特許番号
US05011847

反応ノート

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