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

HRID 510324

反応式

HRID 510324 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 180Acetone溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-bc0e8b82de0849fa90dc3c84ba4aec06
出典データセット
uspto-grants-2015_08
特許番号
US09096607B2

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