Sodium Hydroxide → 3,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzoic acid

HRID 1177221노트

반응식

HRID 1177221 반응식
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:22][CH2:23][O:24][CH3:25])[C:12]=1[CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:8]=[O:9].[OH-:26].[Na+]>CO.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:25][O:24][CH2:23][O:22][C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:12]=1[CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:8]([OH:26])=[O:9]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 866247663,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzaldehyde

생성물 1

HCID 667560413,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzoic acid수율 72.1%

시약·촉매·용매 2

HCID 24470Silver Nitrate촉매HCID 22242641Methanol--water (1/1)용매

실험 절차

To a solution of 3,5-bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzaldehyde (220f) (42 g, 0.12 mol) in MeOH/H2O (500 mL) was added AgNO3 (21 g, 0.12 mol), followed by NaOH (15 g, 0.36 mol) in one portion at room temperature. The mixture was stirred at room temperature overnight and then filtered. The filtrate was concentrated under vacuum to remove MeOH. The residue was extracted with Et2O (2×100 mL) to remove impurities. The aqueous layer was acidified with conc. HCl to pH 4. The resulting white solid was filtered and dried under vacuum to give the title compound (31 g, 62% yield) as white solid.

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under vacuum
  3. customto remove MeOH
  4. extractionThe residue was extracted with Et2O (2×100 mL)
  5. customto remove impurities
  6. filtrationThe resulting white solid was filtered
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-05374786f0c84ef18be21ba93ce6164a
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

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