4-Hydroxybenzaldehyde → HCID 12437011, compound

HRID 2212795Notes

Reaction equation

HRID 2212795 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]([O:12][CH2:13][CH3:14])=[CH2:11].Cl.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C>[CH2:10]([O:12][CH2:13][CH2:14][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH3:11]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 8023Ethyl vinyl etherHCID 10340Sodium Carbonate

Product 1

HCID 12437011HCID 12437011, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 24.4 g (0.2 mole) of 4-hydroxy benzaldehyde in 200 ml of ethyl acetate, 21.6 g (0.3 mole) of ethyl vinyl ether and 0.2 ml (2 millimole) of hydrochloric acid were added, and the mixture was stirred overnight at room temperature. Then, after adding Na2CO3 aqueous solution to neutralize, the mixture was separated and the upper layer was washed with water until pH thereof reached 7. After adding MgSO4 to dry, the mixture was filtered, concentrated and dried, and distilled under reduced pressure to obtain EEBA (100–105° C./0.4 mmHg). Amount obtained was 20 g (yield was 50%).

Workup

  1. additionwere added
  2. customthe mixture was separated
  3. washthe upper layer was washed with water until pH
  4. additionAfter adding MgSO4
  5. customto dry
  6. filtrationthe mixture was filtered
  7. concentrationconcentrated
  8. customdried
  9. distillationdistilled under reduced pressure
  10. customto obtain EEBA (100–105° C./0.4 mmHg)
  11. customAmount obtained

Sources & evidence

ORD record
ord-5ad6f65a871347519706d59796dbb741
Source dataset
uspto-grants-2006_09
Patent number
US07105272B2

Reaction notes

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