Hydrochloric Acid → HCID 19863826, compound

HRID 1165100Notes

Reaction equation

HRID 1165100 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][C:8]([OH:11])=[CH:7][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](=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=2)[O:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 54539569HCID 54539569, compound

Product 1

HCID 19863826HCID 19863826, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,3-benzenediol (870 mg; 2.24 mmole) and conc. hydrochloric acid (2.0 ml) in methanol (15 ml) was heated under reflux for 4 hours, then the reaction solution was poured into 70 ml of water and was extracted twice with isopropyl ether (50 ml). The extract was washed with 100 ml of water (twice) and 100 ml of saturated aqueous solution of sodium chloride (once), followed by drying it over anhydrous magnesium sulfate, distilling off the solvent and subjecting the resultant residue to silica gel column chromatography to thus obtain 610 mg of the title compound from the fractions eluted with hexane-ethyl acetate (10:1). Yield=70%.

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionwas extracted twice with isopropyl ether (50 ml)
  3. washThe extract was washed with 100 ml of water (twice) and 100 ml of saturated aqueous solution of sodium chloride (once),
  4. dry with materialby drying it over anhydrous magnesium sulfate
  5. distillationdistilling off the solvent
  6. washeluted with hexane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-4e1465766be14dd39a17097936b2bc2f
Source dataset
uspto-grants-1990_03
Patent number
US04906669

Reaction notes

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