Methanol → 4-Methoxy-2-methyl-1-naphthol

HRID 1003121

反応式

HRID 1003121 の反応式
S(=O)(=O)(O)O.[CH3:6][C:7]1[C:8](=[O:18])[C:9]2[C:14]([C:15](=[O:17])[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.[CH3:19]O>[Zn].C1(C)C=CC=CC=1>[CH3:19][O:17][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:18])=[C:7]([CH3:6])[CH:16]=1

参加物

6

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4055Menadione

生成物 1

HCID 123598914-Methoxy-2-methyl-1-naphthol収率 81%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

4.9 g of concentrated sulfuric acid were added dropwise to a stirred mixture of 4.75 g (27.6 mmole) of 2-methyl-1,4-naphthoquinone, 2.71 g (41.4 mmole) of zinc powder, 15 mL of methanol and 15 mL of toluene, in an ice bath. After the addition was complete, the reaction mixture was stirred for 4.5 hours at 60° C. The reaction product was extracted with ethyl acetate, washed with water then brine, dried over sodium sulfate, filtered, then evaporated under reduced pressure to yield 4.25 gm (81% yield) of the title compound as an off-white powder having a melting point of 102-103° C. and an 1HNMR as follows: (300 MHz, DMSO-d6) δ 2.38 (s, 3H), 3.91 (s, 3H), 6.76 (s, 1H), 7.42(m, 2H), 8.04 (d, 1H, J=8.1 Hz), 8.14 (d, 1H, J=8.1 Hz), 8.50(bs, 1H). The mass spectrum showed a molecular ion at m/z 188.

後処理

  1. additionAfter the addition
  2. extractionThe reaction product was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-5a1e5779eeb943a3aed850e2da9335e4
出典データセット
uspto-grants-2000_04
特許番号
US06045590

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