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

HRID 1158463노트

반응식

HRID 1158463 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d08a89f71cd84b409999c5fb89fe91c9
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807709B2

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