Ethylene carbonate → 4-(2-Hydroxyethoxy)-3-methylbenzaldehyde

HRID 1846309Notes

Reaction equation

HRID 1846309 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[K+].[K+].[O:17]1[CH2:21][CH2:20]OC1=O>CN(C=O)C>[CH3:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:1][CH2:20][CH2:21][OH:17])[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 1

HCID 791110334-(2-Hydroxyethoxy)-3-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-hydroxy-3-methylbenzaldehyde (0.50 g, 3.67 mmol) in anhydrous DMF (8 mL) was added K2CO3 (1.01 g, 7.34 mmol) and 1,3-dioxolan-2-one (0.65 g, 7.34 mmol), and the mixture was stirred at 110° C. for 60 hours under nitrogen. DMF was removed under vacuum, the residue was diluted with water (50 mL) and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4 and concentrate under vacuum to give 3-methyl-4-hydroxylethoxybenzaldehyde as a yellow oil. Yield: 0.60 g (91%).

Workup

  1. customDMF was removed under vacuum
  2. additionthe residue was diluted with water (50 mL)
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-d3e7a941b4f64259be53f2a7f598fbb4
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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