Water → Methyl 2-(4-formylphenyl)acetate

HRID 339939노트

반응식

HRID 339939 반응식
C[N+]1([O-])CC[O:5]CC1.Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=1.O>CC#N.C1(C)C=CC=CC=1>[CH:10]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=1)=[O:5]

참가 물질

6

반응물 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetate

생성물 1

HCID 19363032Methyl 2-(4-formylphenyl)acetate

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 6342Acetonitrile용매

실험 절차

To a mixture of N-methylmorpholine-N-oxide (63.9 g, 545 mmol) in MeCN (848 g) and toluene (742 g), was added a solution of methyl [4-(bromomethyl)phenyl]acetate (53.0 g) in toluene (212 g) at 0 to 25° C. After stirring for 5 hr, water (106 g) was added to the reaction mixture. The aqueous layer was removed and remaining MeCN in the organic layer was removed under reduced pressure. The remaining toluene solution was washed with water twice (530 g×2), and concentrated under reduced pressure at a temperature below 40° C. until the weight of the solution was 233 g. An activated charcoal (3 g) was added to the solution and removed by filtration. To the solution was added 2,6-dibutyl-4-hydroxytoluene (152 mg), and concentrated under reduced pressure to give the subtitle compound. Yield 30.9 g, 79% from methyl [4-(bromomethyl)phenyl]acetate; 1H NMR (DMSO-d6) δ 9.99 (s, 1H), 7.87 (d, 2H), 7.86 (d, 2H), 3.83 (s, 2H), 3.63 (s, 3H)

후처리

  1. customThe aqueous layer was removed
  2. customwas removed under reduced pressure
  3. washThe remaining toluene solution was washed with water twice (530 g×2)
  4. concentrationconcentrated under reduced pressure at a temperature below 40° C. until the weight of the solution
  5. additionAn activated charcoal (3 g) was added to the solution
  6. customremoved by filtration
  7. additionTo the solution was added 2,6-dibutyl-4-hydroxytoluene (152 mg)
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-03484f212d3d478bbb1253f055dc89be
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895570B2

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