Water → Methyl 2-isopropoxy-4-methoxybenzoate

HRID 34959

反応式

HRID 34959 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:14][C:15](C)([O-])[CH3:16].[K+].BrC(C)C.O>CS(C)=O.C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([O:13][CH:15]([CH3:16])[CH3:14])[CH:4]=1

参加物

7

反応物 4

HCID 962WaterHCID 63582-BromopropaneHCID 79523Methyl 4-methoxysalicylateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 14276512Methyl 2-isopropoxy-4-methoxybenzoate

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
25 °C

実験手順

A solution of 10.0 g (54.9 mmol) methyl 4-methoxysalicylate in 35 ml of dimethyl sulfoxide is treated dropwise with 7.4 g (65.9 mmol) of potassium t-butoxide in 75 ml of dimethylsulfoxide. The resulting pale yellow solution is stirred at 25° C. under nitrogen for 70 minutes. Then 19.7 g (159.8 mmol) of 2-bromopropane is added and the resulting mixture is stirred at 25° C. for 70 hours. The reaction mixture is poured onto 400 ml of H2O and the resulting solution is extracted with diethyl ether (3×125 ml). The combined extracts are washed with aqueous saturated NaCl, dried (Na2SO4) and concentrated in vacuo to give 8.5 g of the crude product as a yellow oil. Flash chromatography (SiO2, 18×65 cm, 15% ethyl acetate-hexane) gives 7.45 g (12.31 g theoretical, 61%) of analytically pure methyl 4-methoxy-2-(1-methylethoxy)benzoate as a colorless oil.

後処理

  1. stirringthe resulting mixture is stirred at 25° C. for 70 hours
  2. extractionthe resulting solution is extracted with diethyl ether (3×125 ml)
  3. washThe combined extracts are washed with aqueous saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give 8.5 g of the crude product as a yellow oil

出典と根拠

ORDレコード
ord-0268e7a1fd674f89a162104e51682dca
出典データセット
uspto-grants-1988_08
特許番号
US04764525

関連ノート

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