Potassium Iodide → HCID 58231421, compound

HRID 1424744Notes

Reaction equation

HRID 1424744 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([OH:12])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(C)=O.O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([O:12][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 579787Methyl 3,5-dihydroxyphenylacetate

Product 1

HCID 58231421HCID 58231421, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of methyl[3,5-dihydroxyphenyl]acetate (2.1 g, 11.5 mmol) in acetone (100 mL) was treated with potassium carbonate (2.4 g, 17.4 mmol), potassium iodide (0.38 g, 2.31 mmol) and benzyl bromide (1.5 mL, 12.7 mmol), and the mixture was stirred at room temperature overnight. The reaction was diluted with water, and was extracted with dichloromethane (×3). Combined organic extracts were dried over sodium sulfate and evaporated in vacuo. The crude material was purified on a Biotage™ 40M column (silica), eluting with 40% ethyl acetate/hexane, to give methyl[3-benzyloxy-5-hydroxyphenyl]acetate (1.0 g, 33%). 1H NMR (400 MHz, CDCl3): δ 7.32-7.42 (m, 5H), 6.48

Workup

  1. extractionwas extracted with dichloromethane (×3)
  2. dry with materialCombined organic extracts were dried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe crude material was purified on a Biotage™ 40M column (silica)
  5. washeluting with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-11441d71cf6f482497f2aea63e898cf6
Source dataset
uspto-grants-2015_01
Patent number
US08927765B2

Reaction notes

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