Acetosyringone → 4-(4-Acetyl-2,6-dimethoxyphenoxy)butanoic acid

HRID 964433

반응식

[C:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([OH:12])=[C:6]([O:13][CH3:14])[CH:5]=1)(=[O:3])[CH3:2].Br[CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20]>>[C:1]([C:4]1[CH:5]=[C:6]([O:13][CH3:14])[C:7]([O:12][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:8]([O:10][CH3:11])[CH:9]=1)(=[O:3])[CH3:2]

참가 물질

반응물 2

HCID 17198Acetosyringone

HCID 76300Ethyl 4-bromobutyrate

생성물 1

HCID 544557414-(4-Acetyl-2,6-dimethoxyphenoxy)butanoic acid

실험 절차

Utilizing the procedure of Preparation 3, 2.61 g (13.32 mmol) of 4-acetyl-2,6-dimethoxyphenol is treated with ethyl 4-bromobutyrate. This gives the desired product after drying at -70° C., under high vacuum, as a brown oil. This is chromatographed on a column of silica gel, and eluted with a 1:1 mixture of ether/hexane leaving 0.40 g (10%) of 4-(4-acetyl-2,6-dimethoxyphenoxy)butanoic acid, ethyl ester as a colorless oil: IR (neat) 1735, 1675 cm-1 ; 1H-NMR (CDCl3) is consistent with the desired product; MS (FAB) m/e 311.1489 Δ=+0.6 mmμ (M+ +H). Analysis calculated. for C16H22O6 : C, 61.92; H, 7.14; O, 30.94. Found: C, 61.48; H, 7.04; O, 31.48.

출처 및 근거

ORD 기록: ord-93ef1795740e492cb3a86d7bd1791aeb
출처 데이터셋: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05767285

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