3-Methyl-2-buten-1-OL → HCID 86605473, compound

HRID 2102980

Reaction equation

HRID 2102980 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[C:6]([CH3:10])=[CH:5][C:3]=1[OH:4].[CH3:11][C:12]([CH3:16])=[CH:13][CH2:14]O>O1CCOCC1>[CH3:1][C:2]1[C:8]([CH2:14][CH2:13][CH:12]([CH3:16])[CH3:11])=[C:7]([OH:9])[C:6]([CH3:10])=[CH:5][C:3]=1[OH:4]

Participants

4

Reactant 2

HCID 111733-Methyl-2-buten-1-OLHCID 692112,5-Dimethylhydroquinone

Product 1

HCID 86605473HCID 86605473, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,5-Dimethylbenzoquinone (5 g) in ethyl acetate was shaken with an aqueous solution of sodium hydrosulfite. The organic layer was separated, washed, dried and evaporated to yield 2,5-dimethylhydroquinone. To a solution of 2,5-dimethylhydroquinone (5 g), prepared as described above, and 3-methyl-2-buten-1-ol (3.1 g) in dioxane (20 mL) was added BF3-ether (4.5 mL) at room temperature under nitrogen. The solution was stirred at room temperature for one hour, extracted with ethyl acetate, washed with water and dried. The mixture containing starting material and alkylated product was hydrogenated in methanol (100 mL) with 5 drops of concentrated HCl in the presence of Pd/C (10%, 200 mg) at60 psi for 18 hours. Workup and chromatography (silica gel hexane-ethyl acetate 5% to 12%) gave 2 g of the desired product, 2,5-dimethyl-3-(3-methyl-butyl)-hydroquinone.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. customdried
  4. additionThe mixture containing
  5. waitwas hydrogenated in methanol (100 mL) with 5 drops of concentrated HCl in the presence of Pd/C (10%, 200 mg) at60 psi for 18 hours

Sources & evidence

ORD record
ord-e0423c6e2b61468f832782cdc85003c5
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Linked notes

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