4-Hydroxybenzaldehyde → Ethyl 2-(4-formylphenoxy)-2-methylpropanoate

HRID 338794Notes

Reaction equation

HRID 338794 reaction equation
C(O[Na])C.[OH:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.Br[C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[CH:10]([C:9]1[CH:12]=[CH:13][C:6]([O:5][C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7][CH:8]=1)=[O:11]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 178474001HCID 178474001, compound

Product 1

HCID 13134808Ethyl 2-(4-formylphenoxy)-2-methylpropanoateYield 41.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In an ethanol solvent, 1 N ethoxy sodium (NaOEt) (1.1 eq.) was added dropwise to 4-hydroxybenzaldehyde (1.0 eq.) and ethyl α-bromoisobutyrate (1.1 eq.), and the reaction mixture was refluxed. After the ethanol was evaporated, the residual was distributed between ethyl acetate and water, and an organic layer was dried by using MgSO4, filtered, and evaporated. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (8:1) to obtain Compound 97a.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. customAfter the ethanol 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-9465d273e00e468e9afaf57d783dafdc
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Reaction notes

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