Tetrahydrofuran → 4-[Hydroxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]benzoic acid

HRID 496347ノート

反応式

HRID 496347 の反応式
[OH-:1].[Na+].C([O:6][CH:7]([C:16]1C(C)=C(OC)[C:19]([O:25][CH3:26])=[C:18]([O:27][CH3:28])[C:17]=1[O:29][CH3:30])[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)(=O)C.[CH2:31]1[CH2:35][O:34][CH2:33][CH2:32]1>[N+]([O-])([O-])=O.[Ag+]>[OH:6][CH:7]([C:16]1[C:31]([CH3:32])=[C:35]([O:34][CH3:33])[C:19]([O:25][CH3:26])=[C:18]([O:27][CH3:28])[C:17]=1[O:29][CH3:30])[C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:13])=[O:1])=[CH:14][CH:15]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22325308HCID 22325308、化合物

生成物 1

HCID 223252814-[Hydroxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]benzoic acid収率 100%

試薬・触媒・溶媒 1

HCID 24470Silver Nitrate触媒

実験手順

After adding dropwise an aqueous solution (20 ml) of silver nitrate (3.06 g, 18.00 mmol) to an aqueous solution of 1 N sodium hydroxide (36 ml), a solution of 4-[acetoxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]benzaldehyde (2.34 g, 6.00 mmol) obtained in Step 2 of Example 1 in THF (30 ml) was added dropwise and the mixture was stirred at room temperature for 5 hours. The reaction mixture was filtered and the solid was washed with hot water. The filtrate and the wash solution were combined, which was then acidified with concentrated hydrochloric acid and then was extracted with ether. The extract was dried and the solvent was distilled off to yield the title compound (2.3 g, 6.37 mmol, yield 100%).

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with hot water
  3. extractionwas extracted with ether
  4. customThe extract was dried
  5. distillationthe solvent was distilled off

出典と根拠

ORDレコード
ord-322fb19bcf544401b1936520ebc1f2da
出典データセット
uspto-grants-2005_09
特許番号
US06943196B1

反応ノート

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