P-Cresol → Methyl 2-(4-methylphenoxy)phenylacetate

HRID 37222

반응식

HRID 37222 반응식
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.C1OCCOCCOCCOCCOCCOC1.Br[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][C:35]([O:37][CH3:38])=[O:36]>CN(C=O)C>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:1][CH:2]=1

참가 물질

5

반응물 3

HCID 2879P-CresolHCID 2855718-Crown-6HCID 8063364Methyl 2-(2-bromophenyl)acetate

생성물 1

HCID 13729875Methyl 2-(4-methylphenoxy)phenylacetate수율 59.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a suspension of KH (212 mg, 1.0 eq) in DMF (3 mL) was added a solution of p-cresol (200 mg; 1.85 mmol) in DMF (2 mL) followed by 18-crown-6 (50 mg, 0.2 eq). After stirring the reaction 45 minutes until the foaming subsides, a solution of methyl 2-bromophenylacetate (424 mg, 1.0 eq) in DMF (1 mL) was added, resulting in a purple solution that slowly faded to yellow. The reaction mixture was stirred 2.5 hours and was then concentrated in vacuo. The residue was chromatographed on a flash silica column (130×30 mm) eluted with 5% ethyl actate/hexane to yield 281 mg (62%) of the title compound (Rf =0.38, 5% ethyl acetate/hexane).

후처리

  1. customthe reaction 45 minutes until the foaming subsides
  2. customresulting in a purple solution that
  3. stirringThe reaction mixture was stirred 2.5 hours
  4. concentrationwas then concentrated in vacuo
  5. customThe residue was chromatographed on a flash silica column (130×30 mm)
  6. washeluted with 5% ethyl actate/hexane

출처 및 근거

ORD 기록
ord-6e956407de254d9abc56f14dc836e35f
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420133

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