Vanillin → HCID 124125, compound

HRID 1845702Notes

Reaction equation

HRID 1845702 reaction equation
[OH-].[K+].[CH3:3][C:4](=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].O=[CH:14][C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1>CO>[OH:21][C:20]1[CH:22]=[CH:23][C:15]([CH:14]=[CH:3][C:4](=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:16][C:17]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 1183VanillinHCID 131872-NonanoneHCID 14797Potassium Hydroxide

Product 1

HCID 124125HCID 124125, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
35 °C

Procedure

100 g potassium hydroxide were dissolved in 500 g of methanol and heated up to reflux under stirring. A solution of 142 g of nonanone and 152 g of vanillin in 120 g of methanol were subsequently added continuously over a period of 1 hour. After that, the mixture was stirred for further 24 hours at the same temperature. After distilling 400 g of methanol from the mixture in vacuo, 400 g of toluene were added to the remaining residue, and after cooling to approximately 30-40° C. additionally 800 g of water were added. The mixture was then acidified with approximately 380 g of diluted sulphuric acid (20% in water) to a pH value of 4-5. After phase separation, the organic phase was washed with 200 g of water. After distillation, 120 g of the intermediate product 1-(4-hydroxy-3-methoxy-phenyl)-dec-1-en-3-one were obtained. Melting point: 45° C., yield: 42% of theory.

Workup

  1. temperatureheated up
  2. temperatureto reflux
  3. stirringAfter that, the mixture was stirred for further 24 hours at the same temperature
  4. distillationAfter distilling 400 g of methanol from the mixture in vacuo, 400 g of toluene
  5. additionwere added to the remaining residue
  6. additionwere added
  7. customAfter phase separation
  8. washthe organic phase was washed with 200 g of water
  9. distillationAfter distillation

Sources & evidence

ORD record
ord-998b1a0433b34e44a457348a6eba769e
Source dataset
uspto-grants-2015_02
Patent number
US08951507B2

Reaction notes

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