Bromocycloheptane → HCID 23442891, compound

HRID 2119701Notes

Reaction equation

HRID 2119701 reaction equation
[C:1]([O:4][C:5]1[C:6]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=[O:11])(=[O:3])[CH3:2].[H-].[Na+].[Mg].[CH:21]1(Br)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[Cl-].[NH4+]>O1CCCC1>[C:1]([O:4][C:5]1[C:6]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][C:8]([OH:13])=[C:9]([CH:10]([CH:21]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[OH:11])[CH:12]=1)(=[O:3])[CH3:2].[C:14]([C:6]1[C:5]([OH:4])=[CH:12][C:9]([CH:10]([CH:21]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[OH:11])=[C:8]([OH:13])[CH:7]=1)([CH3:15])([CH3:16])[CH3:17]

Participants

8

Reactant 5

HCID 16992BromocycloheptaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 23442870HCID 23442870, compound

Product 2

HCID 23442889HCID 23442889, compoundYield 23%HCID 23442891HCID 23442891, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.36 g of 5-acetoxy-4-t-butyl-2-hydroxybenzaldehyde dissolved in 10 ml of anhydrous tetrahydrofuran was added 0.40 g of oily sodium hydride under nitrogen atmosphere and the mixture was stirred at room temperature for 30 minutes. Then, 23 ml of a Grignard reagent (0.43 M in tetrahydrofuran) which has been prepared from magnesium and cycloheptyl bromide was added dropwise to this reaction mixture and the mixture was stirred at room temperature for 1 hour. Then, the mixture was combined with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layers were washed with saturated brine, then dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 15% ethyl acetate) to give 0.77 g of 4-acetoxy-5-t-butyl-2-(cycloheptylhydroxymethyl)phenol as a colorless oil (yield 23%) and 0.72 g of 5-t-butyl-2-(cycloheptylhydroxymethyl) benzene-1,4-diol as a colorless oil (yield 25%).

Workup

  1. additionwas added dropwise to this reaction mixture
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 15% ethyl acetate)

Sources & evidence

ORD record
ord-186631f7c5d5448184c2191ec61909ab
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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