Hydrochloric Acid → HCID 69739073, compound

HRID 985590Notes

Reaction equation

HRID 985590 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([CH:9]([CH3:11])[CH3:10])=[CH:7][CH:6]=[C:5]([CH3:12])[C:4]=1[OH:13].[CH3:14]C(C)([O-])C.[K+].CI.Cl>C1COCC1.O>[CH3:12][C:5]1[C:4]([O:13][CH3:14])=[C:3]([C:8]([CH:9]([CH3:10])[CH3:11])=[CH:7][CH:6]=1)[CH2:2][OH:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 22506830HCID 22506830, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69739073HCID 69739073, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Hydroxymethyl-6-methyl-3-(1-methylethyl)phenol (37.3 g, 207 mmol) was dissolved in THF (350 ml), and then potassium tert-butoxide (22.1 g, 197 mmol) was added. To the mixture was added methyl iodide (19.7 ml, 311 mmol) at 0° C., and the mixture was stirred at room temperature for 16 hours. The reaction mixture was combined with water, made acidic with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate and purified by column chromatography on a small amount of silica gel which was eluted with ethyl acetate. The solvent was concentrated under reduced pressure, and the residue was crystallized from hexane to obtain 21.7 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. custompurified by column chromatography on a small amount of silica gel which
  5. washwas eluted with ethyl acetate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-9abcdb95930c45e58d6df58e384e528a
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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