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

HRID 1643696ノート

反応式

HRID 1643696 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24470Silver Nitrate触媒HCID 22242641Methanol--water (1/1)溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9d5d96b9c627411894929cfd51c6f9b5
出典データセット
uspto-grants-2012_02
特許番号
US08119624B2

反応ノート

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