Water → 2-(4-(4-Hydroxycyclohexyl)cyclohexyl)-5-n-butyl-1,3-dioxane

HRID 2119280Notes

Reaction equation

HRID 2119280 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[O:19][CH2:18][CH:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][O:15]3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[BH4-].[Na+].O>C(O)C>[OH:1][CH:2]1[CH2:3][CH2:4][CH:5]([CH:8]2[CH2:9][CH2:10][CH:11]([CH:14]3[O:15][CH2:16][CH:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18][O:19]3)[CH2:12][CH2:13]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 234403882-(4-(4-Oxocyclohexyl)cyclohexyl)-5-n-butyl-1,3-dioxane

Product 1

HCID 234403822-(4-(4-Hydroxycyclohexyl)cyclohexyl)-5-n-butyl-1,3-dioxaneYield 37.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

In 50 ml of ethanol was dissolved 3.2 g (9.9 mmol) of the 2-(4-(4-oxocyclohexyl)cyclohexyl)-5-n-butyl-1,3-dioxane, and the solution was cooled down to 0° C. To this solution was added gradually 0.19 g (5.0 mmol) of sodium borohydride such that the liquid temperature did not exceed 15° C., and the mixture was stirred for 1 hour. Water in an amount of 50 ml was added to the reaction mixture, the product thus formed was extracted with ether, the extract was washed with 1N-hydrochloric acid and water in this turn, and the solvent was distilled off. After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=2/1), the solvent was distilled off. The residue was recrystallized from ethanol to give 1.2 g (3.7 mmol) of 2-(4-(4-hydroxy-cyclohexyl)cyclohexyl)-5-n-butyl-1,3-dioxane. Yield of this compound based on 2-(4-(4-oxocyclohexyl)cyclohexyl-5-n-butyl-1,3-dioxane was 37%.

Workup

  1. customdid not exceed 15° C.
  2. customthe product thus formed
  3. extractionwas extracted with ether
  4. washthe extract was washed with 1N-hydrochloric acid and water in this turn
  5. distillationthe solvent was distilled off
  6. customAfter the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=2/1)
  7. distillationthe solvent was distilled off
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-1d35dcb6b4c146cc92fdce69529338b6
Source dataset
uspto-grants-2004_02
Patent number
US06685995B1

Reaction notes

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