Hydrochloric Acid → 2H-1-Benzopyran-3-carboxaldehyde, 8-methoxy-

HRID 726942Notes

Reaction equation

HRID 726942 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:6]([O:7][CH3:8])[C:4]=1[OH:5].[OH-].[Na+].[CH:14]([CH:16]=[CH2:17])=[O:15].O=CC1C=CC=C(OC)C=1O.O.Cl>O>[CH3:8][O:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:3]2[C:4]=1[O:5][CH2:17][C:16]([CH:14]=[O:15])=[CH:2]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7847Acrolein2×HCID 8991o-VanillinHCID 14798Sodium HydroxideHCID 86751974HCID 86751974, compound

Product 1

HCID 424282H-1-Benzopyran-3-carboxaldehyde, 8-methoxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One mole of o-vanillin was stirred with 3 liter H2O and 0.05 mole NaOH. A stream of nitrogen was bubbled through 1.5 moles acrolein and then into the o-vanillin-water mixture. When all the acrolein had been driven into the solution (16 hours) the mixture was acidified with 0.06 mole of HCl and the intermediate product (a light yellow crystalline solid) was filtered off and washed with H2O.

Workup

  1. customhad been driven into the solution (16 hours)
  2. filtrationthe intermediate product (a light yellow crystalline solid) was filtered off
  3. washwashed with H2O

Sources & evidence

ORD record
ord-1ff6e8a1f99e4aa68b3cbeb556c50eae
Source dataset
uspto-grants-1998_01
Patent number
US05712223

Reaction notes

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