Methanol → Methyl 4-(1,1-dimethylethyl)-3-methoxybenzoate

HRID 1158463ノート

反応式

HRID 1158463 の反応式
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].OS(O)(=O)=O.[CH3:21]O>O>[CH3:21][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[C:6]([O:14][CH3:15])[CH:7]=1

参加物

5

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 127397584-tert-Butyl-3-methoxybenzoic acid

生成物 1

HCID 68616936Methyl 4-(1,1-dimethylethyl)-3-methoxybenzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 4-tert-butyl-3-methoxy-benzoic acid (3.00 g, 14.4 mmol; commercially available from Apin, 41226B) in MeOH (30 mL) is added H2SO4 conc. (3 mL) and the mixture is refluxed for 5 hrs. After cooling, the mixture is diluted with water, extracted twice with diethyl ether, the combined organics are dried (Na2SO4) and evaporated to dryness to give the title compound as yellowish oil. MS: 223.0 [M+H]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 6.12 min. 1H-NMR (CDCl3): δ 1.41 (s, 9H), 3.91 (s, 3H), 3.92 (s, 3H), 7.36 (dd, 1H), 7.54 (d, 1H), 7.60 (dd, 1H) ppm.

後処理

  1. temperaturethe mixture is refluxed for 5 hrs
  2. temperatureAfter cooling
  3. extractionextracted twice with diethyl ether
  4. dry with materialthe combined organics are dried (Na2SO4)
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-d08a89f71cd84b409999c5fb89fe91c9
出典データセット
uspto-grants-2010_10
特許番号
US07807709B2

反応ノート

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