Dimethyl Sulfoxide → α,α,3-Trimethylbenzeneacetaldehyde

HRID 1610703노트

반응식

HRID 1610703 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1)([CH3:15])[CH2:13][OH:14].C(N(CC)CC)C>O1CCCC1.O>[CH3:15][C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1)([CH3:11])[CH:13]=[O:14]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 3167582-methyl-2-(3-methylphenyl)propan-1-ol

생성물 1

HCID 16204507α,α,3-Trimethylbenzeneacetaldehyde

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of oxalyl chloride (15.1 g, 119 mmol) in tetrahydrofuran (150 ml) was dropwise added a solution of dimethyl-sulfoxide (16.8 ml, 237 mmol) in tetrahydrofuran (50 ml) at −78° C., and the mixture was stirred for 5 min. A solution of 2-methyl-2-(3-methylphenyl)propan-1-ol (12.99 g, 79.09 mmol) in tetrahydrofuran (80 ml) was added at −78° C., and the mixture was stirred for 15 min. Triethylamine (66.1 ml, 475 mmol) was added thereto, and the mixture was warmed to room temperature. The reaction mixture was poured into water and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give the objective substance.

후처리

  1. stirringthe mixture was stirred for 15 min
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained crude product
  6. customwas purified by silica gel column chromatography (hexane/ethyl acetate=15/1)
  7. customto give the objective substance

출처 및 근거

ORD 기록
ord-202c2c2500a64ed7929d044716c2195e
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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