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

HRID 1003121

반응식

HRID 1003121 반응식
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

참가 물질

6

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4055Menadione

생성물 1

HCID 123598914-Methoxy-2-methyl-1-naphthol수율 81%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 1140Toluene용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5a1e5779eeb943a3aed850e2da9335e4
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06045590

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