Ethanol → Ethyl 2-(4-formyl-2-methoxyphenoxy)-2-methylpropanoate

HRID 1748999Notes

Reaction equation

HRID 1748999 reaction equation
C(O)C.C(O[Na])C.[O:8]=[CH:9][C:10]1[CH:18]=[CH:17][C:15]([OH:16])=[C:12]([O:13][CH3:14])[CH:11]=1.Br[C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C>[CH:9]([C:10]1[CH:18]=[CH:17][C:15]([O:16][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:12]([O:13][CH3:14])[CH:11]=1)=[O:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 1183VanillinHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 178474001HCID 178474001, compound

Product 1

HCID 71497692Ethyl 2-(4-formyl-2-methoxyphenoxy)-2-methylpropanoateYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In a co-solvent including ethanol (3 mL) and DMF (3 mL), IN ethoxy sodium (NaOEt) (2.96 mL, 2.96 mmol) was added dropwise to a solution including vanillin (300 mg, 1.97 mmol) and ethyl α-bromoisobutyrate (0.43 mL, 2.93 mmol), and then, the reaction mixture was heated at a temperature of 80° C. overnight. Ethanol was evaporated, and the residual was distributed between ether and water, and an organic layer was dried, filtered, and evaporated. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (EtOAc) (4:1) to obtain Compound 122a (188.7 mg, 36%).

Workup

  1. customEthanol was evaporated
  2. customan organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-96286daf5a7e44eca3bb9f899c2f9178
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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