Methyl iodide → 4-Butoxy-2-methylbenzoic acid

HRID 69405

반응식

HRID 69405 반응식
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:15]N(C)CCN(C)C.C([Li])(CC)C.CI>C1COCC1.O>[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH3:15])[CH:7]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 729714-Butoxybenzoic acidHCID 178418400CID 53628100

생성물 1

HCID 534398994-Butoxy-2-methylbenzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-90 °C

실험 절차

A mixture of 4-butoxybenzoic acid (10 g), N,N,N′,N′-tetramethylethylenediamine (13.2 g) and THF (75 mL) was cooled to −90° C., and sec-butyllithium (81 mL; 1.4 M in hexane) was added over the course of 30 minutes. After a further 30 minutes, the mixture was warmed to −78° C., and a solution of methyl iodide (12.8 mL) in THF (10 mL) was added dropwise. The reaction solution was allowed to warm to room temperature and the mixture was hydrolyzed with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel. The product with the molecular weight of 208.26 (C12H16O3) was obtained in this way; MS (ESI): 209 (M+H+).

후처리

  1. temperaturethe mixture was warmed to −78° C.
  2. temperatureto warm to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. customThe product with the molecular weight of 208.26 (C12H16O3) was obtained in this way

출처 및 근거

ORD 기록
ord-9dbf2c0103ca4e578abbdbf1db5703e5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822495B2

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