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P-Cresol → Methyl (p-tolyloxy)acetate

HRID 2170624
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HRID 2170624 반응식
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:16][C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C>[C:3]1([CH3:8])[CH:4]=[CH:5][C:6]([O:7][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:1][CH:2]=1
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참가 물질

5

반응물 3

HCID 2879P-CresolHCID 10796Cesium carbonateHCID 60984Methyl bromoacetate

생성물 1

HCID 601946Methyl (p-tolyloxy)acetate수율 90.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of p-cresol (2 mL, 19.1 mmol) in anhydrous DMF (50 mL) were added Cs2CO3 (8.1 g, 24.9 mmol) and methyl bromoacetate (1.9 mL, 20.1 mmol). The suspension was stirred at room temperature for 3 h. After dilution with ethyl acetate, the reaction mixture was washed with a 0.5 N HCl solution, a saturated solution of NaHCO3, and brine, dried on MgSO4, and concentrated. The resulting oil was purified by chromatography on silica gel (Hexane/ethyl acetate 8/2) to afford the title compound as a colorless oil (3.10 g, 90%).

후처리

  1. washAfter dilution with ethyl acetate, the reaction mixture was washed with a 0.5 N HCl solution
  2. dry with materiala saturated solution of NaHCO3, and brine, dried on MgSO4
  3. concentrationconcentrated
  4. customThe resulting oil was purified by chromatography on silica gel (Hexane/ethyl acetate 8/2)

출처 및 근거

ORD 기록
ord-9ea61e8b2b854397a161c8d1f54b162f
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051265B2

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