Methyl bromoacetate → 1,1-Bis-(4-hydroxyphenyl)-1-(4-methoxycarbonylmethoxyphenyl)ethane

HRID 510324

반응식

HRID 510324 반응식
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH3:15])=[CH:10][CH:9]=1>[I-].[K+].CC(C)=O>[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[CH:25][CH:24]=2)[CH3:15])=[CH:10][CH:9]=1

참가 물질

5

반응물 2

HCID 60984Methyl bromoacetateHCID 931181,1,1-Tris(4-hydroxyphenyl)ethane

생성물 1

HCID 117178131,1-Bis-(4-hydroxyphenyl)-1-(4-methoxycarbonylmethoxyphenyl)ethane수율 85.1%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 180Acetone용매

실험 절차

Methyl bromoacetate (0.48 mL, 5 mmol) was added dropwise to an acetone solution (10 mL) including 1,1,1-tris(4-hydroxyphenyl)ethane (1.53 g, 5 mmol) potassium carbonate (0.79 g, 5 mmol) and potassium iodide (16 mg, 0.1 mmol). The addition was done at room temperature under argon. The mixture was refluxed for 24 h, and then it was cooled to room temperature and extracted with ethyl acetate. The combined organic layer was washed with 3% aqueous NaHCO3, a saturated brine solution, dried (Na2SO4) and then evaporated to dryness to give 1.61 g (85% yield) of the desired compound as a colorless semisolid. 1H-NMR (300 MHz, d6-DMSO): 1.96 [s, 3H, —CH3], 3.67 [s, 3H, —OCH3], 4.71 [s, 4H, —OCH2—], 6.57-6.64 [m, 4H, Ar—H], 6.72-6.81 [m, 6H, Ar—H], 6.85-6.92 [m, 2H, Ar—H].

후처리

  1. additionThe addition
  2. customwas done at room temperature under argon
  3. temperatureThe mixture was refluxed for 24 h
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer was washed with 3% aqueous NaHCO3
  6. dry with materiala saturated brine solution, dried (Na2SO4)
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-bc0e8b82de0849fa90dc3c84ba4aec06
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096607B2

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