Sulfuric Acid → tert-Butyl 3-acetylbenzoate

HRID 2300769ノート

反応式

HRID 2300769 の反応式
[O-]S([O-])(=O)=O.[Mg+2].OS(O)(=O)=O.[C:12]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([OH:20])=[O:19])(=[O:14])[CH3:13].[C:24](O)([CH3:27])([CH3:26])[CH3:25].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:12]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([O:20][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:19])(=[O:14])[CH3:13]

参加物

7

反応物 5

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2203243-Acetylbenzoic acidHCID 516892Sodium Bicarbonate

生成物 1

HCID 46941403tert-Butyl 3-acetylbenzoate収率 71.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a dry flask under nitrogen, MgSO4 (23.3 mmol) was suspended in CH2Cl2 (23 mL), the mixture was stirred vigorously as concentrated H2SO4 (5.85 mmol) was added dropwise. The resultant mixture was stirred for 20 min and 3-acetylbenzoic acid (5.84 mmol) was added in one portion followed by the dropwise addition of tert-butanol (29.3 mmol). This mixture was stoppered tightly and stirred at room temperature for 114 hours. Worked up by adding 100 mL saturated aqueous NaHCO3 and extracting 3× with 50 mL diethyl ether. The combined extracts were washed with brine, dried over MgSO4 and concentrated. Purified the residue by silica gel chromatography (90:10 hexanes:ethyl acetate) to yield 924 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.56 (m, 1H); 8.20 (m, 1H); 8.14 (m, 1H); 7.55 (t, J=7.6 Hz, 1H); 2.67 (s, 3H); 1.64 (s, 9H).

後処理

  1. additionwas added dropwise
  2. extractionextracting 3× with 50 mL diethyl ether
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurified the residue by silica gel chromatography (90:10 hexanes:ethyl acetate)

出典と根拠

ORDレコード
ord-e1f8fbb219024e19a444de9c99b0d040
出典データセット
uspto-grants-2002_12
特許番号
US06498165B1

反応ノート

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