Water → Methyl 3-(propan-2-yloxy)-2-(prop-2-en-1-yloxy)benzoate

HRID 577563Notes

Reaction equation

HRID 577563 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[C:17]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].[CH2:22](Br)[CH:23]=[CH2:24].O>CN(C)C=O>[CH3:20][CH:19]([O:18][C:17]1[C:8]([O:7][CH2:24][CH:23]=[CH2:22])=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 85741171Methyl 2-hydroxy-3-(propan-2-yloxy)benzoate

Product 1

HCID 86723788Methyl 3-(propan-2-yloxy)-2-(prop-2-en-1-yloxy)benzoateYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (2.05 g, 6.2 mmol) was added to a solution of methyl 2-hydroxy-3-(propan-2-yloxy)benzoate (123c, 539 mg, 2.40 mmol) in N,N-dimethylformamide (9.6 mL), causing a thick paste to form. Allyl bromide (0.25 mL, 3.0 mmol) was added and the mixture stirred at room temperature for 1.5 hours. Deionized water (15 mL) was added, and the solution extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered, concentrated under vacuum, and purified by column chromatography (ethyl acetate/heptane) to give methyl 3-(propan-2-yloxy)-2-(prop-2-en-1-yloxy)benzoate (123d, 474.5 mg, 79% yield) as a colorless oil.

Workup

  1. customto form
  2. extractionthe solution extracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. custompurified by column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-75baa4d631784dc8bf38dd96ac0c6dbf
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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