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

HRID 338811Notes

Reaction equation

HRID 338811 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), 1N 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. additionwas added dropwise to a solution
  2. customEthanol was evaporated
  3. customan organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-76c93a2b72fa484199a5e435a84d3fb4
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Reaction notes

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