Water → HCID 22467107, compound

HRID 1934762Notes

Reaction equation

HRID 1934762 reaction equation
[Mg].[C:2]([C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[CH2:13]1[O:23][C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14]1.O>C(OCC)C.O1CCCC1.C(O)(=O)C>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:19]2([OH:22])[CH2:20][CH2:21][C:16]3([O:23][CH2:13][CH2:14][O:15]3)[CH2:17][CH2:18]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 775951-Bromo-4-tert-butylbenzeneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5462224Magnesium

Product 1

HCID 22467107HCID 22467107, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of nitrogen, 0.23 g of magnesium powder was suspended in 2 ml of anhydrous ethyl ether. While refluxing the suspension, a solution of 2.00 g of 4-tert-butyl-1-bromobenzene in 10 ml anhydrous ethyl ether was dropwise added. After stirring the resulting mixture under reflux for one hour, a solution of 1.17 g of 1,4-cyclohexandione monoethylene ketal in 10 ml anhydrous tetrahydrofuran was dropwise added at 0-5° C., and the temperature was elevated to ambient temperature. After stirring the mixture at the same temperature as above, the reaction mixture was poured into a mixture of water and acetic acid, stirred at ambient temperature for 20 minutes, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by column chromatography [eluent: hexane:ethyl acetate=3:1] gave 1.25 of 8-[4-(tert-butyl)phenyl]-1,4-dioxaspiro[4.5]decan-8-ol as a light yellow oily product.

Workup

  1. temperatureWhile refluxing the suspension
  2. temperatureunder reflux for one hour
  3. customwas elevated to ambient temperature
  4. stirringAfter stirring the mixture at the same temperature as above, the reaction mixture
  5. stirringstirred at ambient temperature for 20 minutes
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customPurification of the residue by column chromatography [eluent: hexane:ethyl acetate=3:1]

Sources & evidence

ORD record
ord-a443625fe5794a98a310111b4c17b34a
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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