p-Toluenesulfonic acid → Methyl 3,5-dihydroxy-4-methylbenzoate

HRID 555167

반응식

HRID 555167 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:12])[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[CH3:13]C1C=CC(S(O)(=O)=O)=CC=1>CO>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:12])[C:10]=1[CH3:11])[C:5]([O:7][CH3:13])=[O:6]

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 27480453,5-Dihydroxy-4-methylbenzoic Acid

생성물 1

HCID 11458051Methyl 3,5-dihydroxy-4-methylbenzoate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

3,5-Dihydroxy-4-methylbenzoic acid (5.0 g, 29.79 mmol, 1.0 eq) and PTSA (1.13 g, 5.94 mmol, 0.2 eq) were dissolved in 50 ml of methanol, and the mixture was heated to reflux for 6 h. Methanol was evaporated. The resultant solid was washed with 10% sodium bicarbonate solution. The aqueous solution was extracted thrice with ethyl acetate. The combined organic layer was dried over sodium sulphate and evaporated under vacuum. Yield: 5.25 g (96%). 1H NMR (400 MHz, DMSO-d6): δ 1.98 (s, 3H), 3.78 (s, 3H), 6.93 (s, 2H), 9.53 (s, 2H). LCMS: (ES+) m/z=183 (M+H) Method: Column: PHENOMENEX® Luna C18 (4.6×30) mm, 5 micron. Mphase A: 10% MeOH-90% H2O-10 mM NH4OAc. Mphase B: 90% MeOH-10% H2O-10 mM NH4OAc. Flow: 5 ml/min

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 h
  3. customMethanol was evaporated
  4. washThe resultant solid was washed with 10% sodium bicarbonate solution
  5. extractionThe aqueous solution was extracted thrice with ethyl acetate
  6. dry with materialThe combined organic layer was dried over sodium sulphate
  7. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-f13df86490824119ad650454f82e7374
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048887B2

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