HCID 13956354, compound → HCID 54551386, compound

HRID 981590Notes

Reaction equation

HRID 981590 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([CH3:13])=[CH:5][C:4]=1[OH:14].O[CH2:16][CH:17]=[C:18]([CH3:27])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:26])[C:23]([OH:25])=[O:24]>C1C=CC=CC=1>[C:23]([C:22]([CH3:26])=[CH:21][CH2:20][CH2:19][C:18]([CH3:27])=[CH:17][CH2:16][C:5]1[C:4]([OH:14])=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]=1[CH3:13])([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 13956354HCID 13956354, compoundHCID 54313026HCID 54313026, compound

Product 1

HCID 54551386HCID 54551386, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5 g of 2,3,4-trimethoxy-5-methylphenol was dissolved in 10 ml of benzene and 10 g of silica alumina was added thereto. 1.8 g of 8-hydroxy-2,6-dimethyl-2,6-octadienoic acid dissolved in 4 ml of benzene was added to the above solution. The obtained solution was heated to 40° to 50° C. for two hours to allow reaction. The reaction mixture was then filtered and the precipitate was washed with ethyl ether while the filtrate was washed with water, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography with the use of ether/n-hexane as the eluent to give 1.3 g of the title compound as a colorless oil.

Workup

  1. addition10 g of silica alumina was added
  2. additionwas added to the above solution
  3. temperatureThe obtained solution was heated to 40° to 50° C. for two hours
  4. customreaction
  5. filtrationThe reaction mixture was then filtered
  6. washthe precipitate was washed with ethyl ether while the filtrate
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe concentrate was purified by silica gel chromatography with the use of ether/n-hexane as the eluent

Sources & evidence

ORD record
ord-6f0a26ab84d2436999a5076cc4d581b2
Source dataset
uspto-grants-1991_02
Patent number
US04992469

Reaction notes

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