Hydrochloric Acid → 4-Hydroxy-4-(4-(4-pentylcyclohexyl) cyclohexyl)butanal propylene acetal

HRID 1857301Notes

Reaction equation

HRID 1857301 reaction equation
Br[CH2:2][CH2:3][CH:4]1[O:9][CH2:8][CH2:7][CH2:6][O:5]1.[Mg].[CH2:11]([CH:16]1[CH2:21][CH2:20][CH:19]([CH:22]2[CH2:27][CH2:26][CH:25]([CH:28]=[O:29])[CH2:24][CH2:23]2)[CH2:18][CH2:17]1)[CH2:12][CH2:13][CH2:14][CH3:15].Cl>O1CCCC1>[CH2:6]1[O:5][CH:4]([CH2:3][CH2:2][CH:28]([OH:29])[CH:25]2[CH2:24][CH2:23][CH:22]([CH:19]3[CH2:20][CH2:21][CH:16]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:17][CH2:18]3)[CH2:27][CH2:26]2)[O:9][CH:8]1[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5206561,3-Dioxane, 2-(2-bromoethyl)-HCID 5462224MagnesiumHCID 1800049482241-70-1

Product 1

HCID 570666564-Hydroxy-4-(4-(4-pentylcyclohexyl) cyclohexyl)butanal propylene acetalYield 82.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To Grignard reagent prepared from 33.7 g (173 mmol) of 2-(2-bromoethyl)-1,3-dioxane and magnesium in 300 ml of tetrahydrofuran (THF), a solution of 40.0 g (151 mmol) of 4-(4-pentylcyclohexyl) cyclohexane carbaldehyde (10) in 200 ml of THF was added dropwise, and the resultant solution was stirred for 3 hours. The reaction solution was added into 500 ml of 1N-hydrochloric acid, and the reaction product was extracted with 300 ml of toluene. The formed organic layer was sequentially washed with a saturated aqueous solution of hydrogen sodium carbonate and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane) to obtain 47.5 g (125 mmol) of 4-hydroxy-4-(4-(4-pentylcyclohexyl) cyclohexyl)butanal propylene acetal (11) at a yield of 82.8 percent.

Workup

  1. extractionthe reaction product was extracted with 300 ml of toluene
  2. washThe formed organic layer was sequentially washed with a saturated aqueous solution of hydrogen sodium carbonate and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: hexane)

Sources & evidence

ORD record
ord-144a5ca3c7074b02a418fd61661a630b
Source dataset
uspto-grants-2000_11
Patent number
US06146718

Reaction notes

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