Dimethyl Sulfate → 4-Benzyloxy-2-methoxy-3-methyl-benzaldehyde

HRID 929100ノート

反応式

HRID 929100 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:17])[C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19]OS(OC)(=O)=O.[OH-].[Na+].O1CCOCC1>O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([O:17][CH3:19])[C:10]=1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 597616904-(Benzyloxy)-2-hydroxy-3-methylbenzaldehyde

生成物 1

HCID 597617644-Benzyloxy-2-methoxy-3-methyl-benzaldehyde

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
90 °C

実験手順

A mixture of 4-benzyloxy-2-hydroxy-3-methyl-benzaldehyde (1.57 g, 6.49 mmol), dimethylsulfate (1.04 ml, 10.9 mmol), NaOH (1.02 g, 25.5 mmol), 1,4-dioxane (20 mL) and water (10 mL) was stirred at 90° C. for 6 h. The reaction mixture was cooled to RT, water (100 mL) was added, extracted with EtOAc (150 mL). The extract was washed with brine (100 mL), dried over Na2SO4 and evaporated. The residue was purified on SiO2 (25 g) column, hexane to toluene. Yield 1.20 g (4.68 mmol, 72%), white solid. 1H NMR (300 MHz, DMSO): δ 10.11 (s, 1H), 7.64 (d, J=8.9 Hz, 1H), 7.49-7.32 (m, 5H), 7.05 (d, J=8.9 Hz, 1H), 5.24 (s, 2H), 3.81 (s, 3H), 2.14 (s, 3H).

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with EtOAc (150 mL)
  3. washThe extract was washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified on SiO2 (25 g) column, hexane to toluene

出典と根拠

ORDレコード
ord-17635ebc867d4da2906c01b4a6573843
出典データセット
uspto-grants-2016_03
特許番号
US09290503B2

反応ノート

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