Dimethylformamide → 2,4-Dihydroxy-3-methylbenzaldehyde

HRID 561915

反応式

HRID 561915 の反応式
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][C:8]=1[OH:9].CN([CH:18]=[O:19])C>[OH-].[Na+]>[OH:9][C:8]1[C:7]([CH3:6])=[C:13]([OH:14])[CH:12]=[CH:11][C:10]=1[CH:18]=[O:19]

参加物

5

反応物 3

HCID 6228Dimethylformamide2 回HCID 118432-MethylresorcinolHCID 24813Phosphorus oxychloride

生成物 1

HCID 803952,4-Dihydroxy-3-methylbenzaldehyde

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

Phosphorus oxychloride (8.0 mL, 86 mmol) was added dropwise with stirring to DMF (26 mL, 0.336 mol) the temperature being kept at 10-20° C. This reagent was slowly added to a solution of 2-methylresorcinol (4.84 g, 39 mmol) in 26 mL DMF at 20-30° C. After 30 min the reaction mixture was poured in 2 M aq. NaOH (200 ml), extracted with Et2O (2×100 mL), aqueous phase was neutralized with 5N aq. HCl, the product was extracted with Et2O (2×200 mL), dried and evaporated. The residue was separated on SiO2 (100 g) column, hexane-EtOAc (0 to 20% v/v). Yield 4.1 g (27 mmol, 69%) as white solid. 1H NMR (300 MHz, DMSO): δ 11.61 (s, 1H), 10.79 (s, 1H), 9.71 (s, 1H), 7.43 (d, J=8.4 Hz, 1H), 6.55 (d, J=8.5 Hz, 1H), 1.97 (s, 3H).

後処理

  1. custombeing kept at 10-20° C
  2. extractionextracted with Et2O (2×100 mL), aqueous phase
  3. extractionthe product was extracted with Et2O (2×200 mL)
  4. customdried
  5. customevaporated
  6. customThe residue was separated on SiO2 (100 g) column, hexane-EtOAc (0 to 20% v/v)

出典と根拠

ORDレコード
ord-b1a0f54e44cd4e49bd367b78c935501a
出典データセット
uspto-grants-2011_11
特許番号
US08063225B2

関連ノート

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