Hydrochloric Acid → 4-Benzyloxy-3-methoxyphenylacetic Acid

HRID 467035

반응식

HRID 467035 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18]CC)=[O:17])=[CH:11][C:10]=1[O:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[OH-].[Li+].Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][C:10]=1[O:21][CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 13891550Ethyl 4-benzyloxy-3-methoxyphenylacetate

생성물 1

HCID 2979644-Benzyloxy-3-methoxyphenylacetic Acid수율 58%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of ethyl 4-benzyloxy-3-methoxyphenylacetate (32 g, 110 mmol), from Step 1, in ethanol (200 mL) and THF (20 mL) was added 200 mL of a 1M aqueous lithium hydroxide solution. The resulting mixture was stirred at ambient temperature for 4 hours and then 1M aqueous hydrochloric acid solution was added to precipitate the product. The solid was filtered, washed with water, taken up in diethyl ether, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound as a yellow solid. The solid was recrystallized from methylene chloride/petroleum ether (b.p. 30°-60° C.) to give 19 g (58% yield based on ethyl 4-hydroxy-3-methoxyphenylacetic acid) of the title compound as a white solid; 1H NMR (CDCl3) δ 3.57 (s, 2H), 3.88 (s, 3H), 5.14 (s, 2H), 6.74 (dd, 1H, J=8.0, 2.7 Hz), 6.82-6.85 (m, 2H), 7.28-7.45 (m, 5H).

후처리

  1. customto precipitate the product
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9369537eaab2497f95ae60a8e1441ccc
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05158948

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