HCID 13956354, compound → HCID 53757659, compound

HRID 981591Notes

Reaction equation

HRID 981591 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]([CH3:37])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:36])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:35])[CH2:27][CH2:28][CH:29]=[C:30]([CH3:34])[C:31]([OH:33])=[O:32]>C1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[C:31]([C:30]([CH3:34])=[CH:29][CH2:28][CH2:27][C:26]([CH3:35])=[CH:25][CH2:24][CH2:23][C:22]([CH3:36])=[CH:21][CH2:20][CH2:19][C:18]([CH3:37])=[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:33])=[O:32]

Participants

5

Reactant 2

HCID 13956354HCID 13956354, compoundHCID 53740698HCID 53740698, compound

Product 1

HCID 53757659HCID 53757659, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent2×

Procedure

5 g of 2,3,4-trimethoxy-5-methylphenol was dissolved in 10 ml of benzene and 6 g of silica gel (Wako gel C-200) and 3 g of zinc chloride were added thereto. 3 g of 16-hydroxy-2,6,10,14-tetramethyl-2,6,10,14-hexadecatetraenoic acid dissolved in 5 ml of benzene was added to the above solution. After reacting at room temperature for 30 min, the reaction mixture was filtered and the precipitate was washed with ethyl ether while the filtrate was washed with water, dried over magnesium sulfate anhydride and concentrated. The concentrate was purified by means of silica gel chromatography with the use of ether/n-hexane as the eluent to give 2.1 g of the title compound as a colorless oil.

Workup

  1. additionwas added to the above solution
  2. filtrationthe reaction mixture was filtered
  3. washthe precipitate was washed with ethyl ether while the filtrate
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate anhydride
  6. concentrationconcentrated
  7. customThe concentrate was purified by means of silica gel chromatography with the use of ether/n-hexane as the eluent

Sources & evidence

ORD record
ord-ddd9e4fa05154d158473650616e00fbc
Source dataset
uspto-grants-1991_02
Patent number
US04992469

Reaction notes

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