Phenol → 3,5-Di-tert-butylsalicylaldehyde

HRID 258208

反応式

HRID 258208 の反応式
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:18]1([OH:24])C=CC=CC=1.C(Cl)(Cl)Cl>C(O)C.O.S(=O)(=O)(O)O>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:18]=[O:24])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 996PhenolHCID 6212ChloroformHCID 73112,4-Di-tert-butylphenolHCID 14798Sodium Hydroxide

生成物 1

HCID 6880233,5-Di-tert-butylsalicylaldehyde収率 33%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 1118Sulfuric Acid溶媒

実験手順

2,4-di-t-butylphenol (75 g, 0.36 mole) was dissolved in 200 ml absolute ethanol in a 1 L round bottom flask equipped with a water-cooled condenser. Sodium hydroxide (82 g, 2.0 moles) was dissolved in 80 ml water and added while still hot to the solution of phenol. Chloroform (156 g, 1.31 mole) was added in 2 ml portions over a 45-minute period. The resulting yellow-brown mixture was stirred 1 hour while cooling to ambient temperature. The mixture was diluted with 500 ml of 1M sulfuric acid and extracted with 200 ml of dichloromethane. The organic layer was isolated in a separatory funnel and dried over anhydrous magnesium sulfate. The mixture was filtered and rotoevaporated to a thick syrup. The yield was 33%. The IR spectrum of the crude product showed the characteristic aldehyde carbonyl (C=O) stretching frequency at 1648 cm-1. The product was used without further purification.

後処理

  1. temperaturecooled condenser
  2. extractionextracted with 200 ml of dichloromethane
  3. customThe organic layer was isolated in a separatory funnel
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customThe product was used without further purification

出典と根拠

ORDレコード
ord-c0a82c355bd7434d9d23b0a5c3d5b7db
出典データセット
uspto-grants-1993_11
特許番号
US05266283

関連ノート

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