Hydrochloric Acid → HCID 19863839, compound

HRID 1165101Notes

Reaction equation

HRID 1165101 reaction equation
[CH3:1][C:2]([CH2:13][CH2:14][CH2:15][CH:16]([CH3:28])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=1[OH:12].Cl.O>CO>[CH3:1][C:2]1([CH2:13][CH2:14][CH2:15][CH:16]([CH3:28])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:3][CH2:4][C:5]2[C:6](=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=2)[O:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 54546881HCID 54546881, compound

Product 1

HCID 19863839HCID 19863839, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2-benzenediol (1.00 g; 2.57 mmole) and conc. hydrochloric acid (2.0 ml) in 10 ml of methanol were heated under reflux for 4 hours, then the reaction solution was poured into 100 ml of water and was extracted twice with 50 ml of isopropyl ether. The extract was washed twice with 100 ml of water and once with 100 ml of saturated aqueous solution of sodium chloride, followed by drying it over anhydrous magnesium sulfate, distilling off the solvent and subjecting the resulting residue to silica gel column chromatography. Thus, 790 mg of the title compound was recovered from the fractions eluted through the column with hexane-ethyl acetate (30:1). Yield=79%.

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionwas extracted twice with 50 ml of isopropyl ether
  3. washThe extract was washed twice with 100 ml of water and once with 100 ml of saturated aqueous solution of sodium chloride
  4. dry with materialby drying it over anhydrous magnesium sulfate
  5. distillationdistilling off the solvent
  6. customThus, 790 mg of the title compound was recovered from the fractions
  7. washeluted through the column with hexane-ethyl acetate (30:1)

Sources & evidence

ORD record
ord-ab8e81251a5d4dd3a545096713420fe2
Source dataset
uspto-grants-1990_03
Patent number
US04906669

Reaction notes

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