4-tert-Butylphenol → 4-(4-Tert-butylphenoxy)butyl acetate

HRID 5008

반응식

HRID 5008 반응식
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[O-]C1C=CC=CC=1.[C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28]Cl)(=[O:23])[CH3:22]>CN(C)C=O>[C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])=[CH:12][CH:11]=1)(=[O:23])[CH3:22]

참가 물질

6

반응물 4

HCID 73934-tert-ButylphenolHCID 233991-Butanol, 4-chloro-, 1-acetateHCID 24758Sodium hydrideHCID 119047Phenolate2회

생성물 1

HCID 133137364-(4-Tert-butylphenoxy)butyl acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a stirred slurry of 1.6 g sodium hydride (as 50% dispersion in oil) in 50 ml dry dimethyl formamide was added, drop-wise, a solution of 5.0 g p-tert-butylphenol (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution stirred under nitrogen until the phenoxide had totally formed. To the phenoxide was added a solution of 5.0 g 4-chlorobutyl acetate (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution was stirred for fourteen hours. The reaction mixture was partitioned between water/toluene. The organic layer was removed, washed with water, then 1N sodium bicarbonate. The organic layer was removed, dried and evaporated to an orange oil, 5.6 g. The oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent) yielding pure 4-(p-tert-butylphenoxy)-butyl acetate.

후처리

  1. customhad totally formed
  2. customThe reaction mixture was partitioned between water/toluene
  3. customThe organic layer was removed
  4. washwashed with water
  5. customThe organic layer was removed
  6. customdried
  7. customevaporated to an orange oil, 5.6 g
  8. customThe oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent)

출처 및 근거

ORD 기록
ord-cebef95bc8384043b4a84d71a6aab475
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242936

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