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

HRID 1879617Notes

Reaction equation

HRID 1879617 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-ba127a8f883e4087941494f5e855a23a
Source dataset
uspto-grants-2012_11
Patent number
US08318699B2

Reaction notes

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