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

HRID 555167ノート

反応式

HRID 555167 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-f13df86490824119ad650454f82e7374
出典データセット
uspto-grants-2011_11
特許番号
US08048887B2

反応ノート

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