Water → 2,6-Diethyl-4-methylbenzyl alcohol

HRID 385238노트

반응식

HRID 385238 반응식
[CH2:1]([C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH:5]=[O:6])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S(=O)(=O)(O)O>C(OCC)C>[CH2:1]([C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH2:5][OH:6])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 221537982,6-Diethyl-4-methylbenzaldehyde

생성물 1

HCID 667075402,6-Diethyl-4-methylbenzyl alcohol수율 92.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 35.5 g (201.4 mmol) of 2,6-diethyl-4-methylbenzaldehyde, dissolved in 80 ml of diethyl ether is added dropwise to a suspension of 2.10 g (55.4 mmol) of lithium aluminium hydride in 200 ml of diethyl ether. The mixture is then heated at reflux for another 1 h. After cooling, the mixture is hydrolyzed with water and 10% strength sulphuric acid, the phases are separated and the aqueous phase is extracted two more times with diethyl ether. Drying (magnesium sulphate), distillative removal of the solvent and chromatography of the resulting crude product on silica gel (ethyl acetate/hexane=30:70) gives 33.10 g (92%) of 2,6-diethyl-4-methylbenzyl alcohol in the form of colourless crystals of m.p. 71-72° C. 1H-NMR (400 MHz, CDCl3): δ=1.22 (t, 6H), 2.30 (s, 3H), 2.74 (q, 4H), 4.71 (s, 2H), 6.90 (s, 2H).

후처리

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for another 1 h
  3. temperatureAfter cooling
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted two more times with diethyl ether
  6. customDrying
  7. custom(magnesium sulphate), distillative removal of the solvent and chromatography of the resulting crude product on silica gel (ethyl acetate/hexane=30:70)

출처 및 근거

ORD 기록
ord-78777e775d634ce1bb2c4aa1c76e2e94
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367873B2

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