4-[3-Methoxy-4-(methoxymethoxy)phenyl]but-3-en-2-one → 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one

HRID 77672노트

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HRID 77672 반응식
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=1[O:16][CH3:17]>CO.Cl>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=1[O:16][CH3:17]

참가 물질

4

반응물 1

HCID 695016824-[3-Methoxy-4-(methoxymethoxy)phenyl]but-3-en-2-one

생성물 1

HCID 141214-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one수율 74%

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

1-(4-Methoxymethyloxy-3-methoxyphenyl)-1-buten-3-one (35j, 0.40 g, 1.7 mmol) was dissolved in methanol (40 ml) and stirred for 15 min at 50° C. Hydrochloric acid (3 drops) was added and the mixture stirred for 18 hr at 65° C. The methanol was evaporated and the resulting residue extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was chromatographed on silica gel with ethyl acetate/hexane to give 0.24 g (74%) of an orange-yellow solid: mp 120-122° C. [expected mp 128-129° C.]; 1H NMR δ 2.34 (s, 3H), 3.91 (s, 3H), 5.98 (s, 1H), 6.56 (d, 1H, J=16.1 Hz), 6.91 (d, 1H, J=8.2 Hz), 7.04 (m, 2H), 7.43 (d, 1H, J=16.3 Hz); 13C NMR: δ 27.3, 56.0, 109.3, 114.8, 123.4, 124.9, 126.9, 143.6, 146.8, 148.2, 198.2.

후처리

  1. stirringthe mixture stirred for 18 hr at 65° C
  2. customThe methanol was evaporated
  3. extractionthe resulting residue extracted into ethyl acetate
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a solid
  9. customThe crude solid was chromatographed on silica gel with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-5718adf006a54864bb31c397ba939ec5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841326B2

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