Ethyl vinyl ether → 4-[2-(1-Ethoxyethoxy)ethoxy]-3,5-dimethoxybenzaldehyde

HRID 1925795Notes

Reaction equation

HRID 1925795 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:15][CH3:16].[CH:17]([O:19][CH2:20][CH3:21])=[CH2:18].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.C(=O)([O-])O.[Na+].OCCOC1C(OC)=CC(OC)=CC=1C=O>C(Cl)Cl>[CH2:17]([O:19][CH:20]([O:1][CH2:2][CH2:3][O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:15][CH3:16])[CH3:21])[CH3:18]

Participants

7

Reactant 5

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 19622754HCID 19622754, compoundHCID 86642599HCID 86642599, compound

Product 1

HCID 714274724-[2-(1-Ethoxyethoxy)ethoxy]-3,5-dimethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-hydroxyethoxy)-3,5-dimethoxybenzaldehyde (1.5 g, 6.6 mmol) in methylene chloride (22 mL, 0.3 M) was added ethyl vinyl ether (3.4 mL, 19.9 mmol). After addition of PPTS (168 mg, 0.66 mmol), the reaction mixture was stirred for 40 minutes at room temperature. An aqueous saturated sodium hydrogen carbonate solution was added to the reaction fluid, which was then extracted with ethyl acetate, washed with saturated saline, dried over magnesium sulfate, and evaporated under reduced pressure to afford a residue containing an ethoxyethyl-protected 4-(2-hydroxyethoxy-3,5-dimethoxybenzaldehyde.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washwashed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto afford a residue

Sources & evidence

ORD record
ord-7388324ef0c84a059209803809dc1cdd
Source dataset
uspto-grants-2012_05
Patent number
US08178727B2

Reaction notes

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