Hydrochloric Acid → 3-Benzyloxy-p-anisic acid

HRID 2297435ノート

反応式

HRID 2297435 の反応式
[O-:1][Mn](=O)(=O)=O.[K+].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH:18]=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.N1C=CC=CC=1>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:18]([OH:1])=[O:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 516875Potassium Permanganate

生成物 1

HCID 940573-Benzyloxy-p-anisic acid収率 88.5%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒4 回HCID 1049Pyridine溶媒

実験手順

A solution of KMnO4 (24.81 g, 0.157 mole) in water (100 ml) was added under stirring with a solution of tetrabutylammonium bromide (50.61 g, 0.157 mole) in water (200 ml), diluting with further water (200 ml). The solid was separated by filtration, squeezed and dissolved in pyridine (300 ml). The solution was dropped into a solution of 3-benzyloxy-4-methoxy-benzaldehyde (38.2 g, 0.157 mole), prepared as described in example 52, in pyridine (150 ml) in water bath. After 3 hours the mixture was brought to acidic pH with 1N HCl, the solid was filtered off and the mother liquors were extracted more times with CH2Cl2. The organic phase was anhydrified, concentrated and the residue taken up in 1N NaOH and washed with ethyl ether. The aqueous solution was acidified and extracted twice with CH2Cl2, brought to dryness, discoloured with TONSIL® and concentrated to small volume. The precipitate was filtered to give 35.869 g of the title compound (yield: 88%).

後処理

  1. customThe solid was separated by filtration
  2. dissolutiondissolved in pyridine (300 ml)
  3. customprepared
  4. filtrationthe solid was filtered off
  5. extractionthe mother liquors were extracted more times with CH2Cl2
  6. concentrationconcentrated
  7. washwashed with ethyl ether
  8. extractionextracted twice with CH2Cl2
  9. concentrationconcentrated to small volume
  10. filtrationThe precipitate was filtered

出典と根拠

ORDレコード
ord-8f1f8d81374a4874b50dbf647a064049
出典データセット
uspto-grants-2002_12
特許番号
US06492360B1

反応ノート

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