Methanol → Methyl 3,4-Dihydroxy-2-methylbenzoate

HRID 919007노트

반응식

HRID 919007 반응식
[OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([OH:1])[C:3]=1[CH3:12]

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 104420733,4-Dihydroxy-2-methylbenzoic acid

생성물 1

HCID 59016598Methyl 3,4-Dihydroxy-2-methylbenzoate수율 83%

실험 절차

To a round bottom flask equipped with magnetic stirring and a reflux condenser was added 3,4-dihydroxy-2-methylbenzoic acid (23.3 g, 139 mmol), methanol (139 mL), and concentrated sulfuric acid (0.77 mL, 13.9 mmol). This mixture was heated to reflux for 18 hours. The reaction was cooled to room temperature and the methanol evaporated. The residue was taken up in ether and washed once with saturated sodium bicarbonate solution, once with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to give a brown solid, methyl-3,4-dihydroxy-2-methylbenzoate, (20.9 g, 114 mmol) in 83% yield. 1H-NMR (300 MHz, CD3COCD3) δ (ppm): 2.47 (s, 3H), 3.79 (s, 3H), 6.78 (d, 1H), 7.46 (d, 1H); TLC: Rf=0.54 (1:1 ethyl acetate/hexane).

후처리

  1. customTo a round bottom flask equipped
  2. temperatureThis mixture was heated
  3. temperatureto reflux for 18 hours
  4. customthe methanol evaporated
  5. washwashed once with saturated sodium bicarbonate solution, once with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-131b977081b844c4b5201471ca299196
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09272986B2

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