1,4-Cyclohexanediol → t-Butyl (4-hydroxycyclohexyl)acetate

HRID 1291019Notes

Reaction equation

HRID 1291019 reaction equation
[OH-].[Na+].[CH:3]1([OH:10])[CH2:8][CH2:7][CH:6](O)[CH2:5][CH2:4]1.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:10][CH:3]1[CH2:4][CH2:5][CH:6]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 111621,4-CyclohexanediolHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 18919465t-Butyl (4-hydroxycyclohexyl)acetateYield 7,645.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Sodium hydroxide (5.7 g, 0.14 mol) was dissolved in water (6 ml) and 1,4-cyclohexanediol (cis/trans=6/4) (15.0 g, 0.13 mmol) was added, which was followed by stirring at room temperature for 30 minutes. Then, tetrabutylammonium bromide (20.8 g, 0.065 mol) and t-butyl bromoacetate (24.5 ml, 0.13 mol) were added, and the mixture was stirred at room temperature for one hour. The reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1-2/1) to give 2.13 g of t-butyl (4-hydroxycyclohexyl)acetate as a transparent oil (7%).

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration, low boiling matters
  5. distillationwere distilled away from the filtrate under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1-2/1)

Sources & evidence

ORD record
ord-925a5acc21444eae96d778a11499a759
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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