Phenol → 3,5-Di-tert-butylsalicylaldehyde

HRID 258208

반응식

HRID 258208 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 6880233,5-Di-tert-butylsalicylaldehyde수율 33%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매2회HCID 1118Sulfuric Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c0a82c355bd7434d9d23b0a5c3d5b7db
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05266283

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