Ethyl homovanillate → Homovanillic Acid

HRID 2092379노트

반응식

HRID 2092379 반응식
C([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH3:14])[CH:7]=1)C>CO.O>[OH:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:15])=[O:3])=[CH:7][C:8]=1[O:13][CH3:14]

참가 물질

4

반응물 1

HCID 108965Ethyl homovanillate

생성물 1

HCID 1738Homovanillic Acid수율 96.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A mixture of (4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester (2 g, 9.51 mmol) and LiOH monohydrate (1.2 g, 28.5 mmol) in MeOH (20 ml) and water (10 ml) was stirred at RT for 14 h. The reaction mixture was concentrated under vacuum, diluted into water and neutralized by the addition of HCl 2 M in water (14.3 ml). The resulting slurry was extracted with DCM (3×) and AcOEt (2×) and the combined organic fractions were dried over Na2SO4, filtered and evaporated to dryness to yield the crude title compound (1.67 g, 9.17 mmol, 96%) as a brownish solid, which was used in the next step without further purification. HPLC: AtRet=0.77 min; LC-MS: m/z 183.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 3.43 (s, 2H), 3.74 (s, 3H), 6.61-6.66 (m, J=8.1, 2.0, 1H), 6.67-6.72 (m, 1H), 6.81 (d, J=2.0, 1H), 8.81 (s, 1H), 12.17 (s, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additiondiluted into water
  3. additionneutralized by the addition of HCl 2 M in water (14.3 ml)
  4. extractionThe resulting slurry was extracted with DCM (3×) and AcOEt (2×)
  5. dry with materialthe combined organic fractions were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-1d938c49aa6a467293caa955edabafcd
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440693B2

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