Hydrochloric Acid → 2-(4-Propylcyclohexyl)propane-1,3-diol

HRID 1707528Notes

Reaction equation

HRID 1707528 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]([C:16](OCC)=[O:17])[C:11](OCC)=[O:12])[CH2:6][CH2:5]1)[CH2:2][CH3:3].O.Cl>C1(C)C=CC=CC=1>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]([CH2:11][OH:12])[CH2:16][OH:17])[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13561188Diethyl 4-propylcyclohexylmalonate

Product 1

HCID 112294182-(4-Propylcyclohexyl)propane-1,3-diolYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

340 cm] (1.3 mol) of a 70% NaAlH2 (OC2H4OCH3)2 in toluene with 340 cm3 of anhydrous toluene was stirred at room temperature while adding 57 g (0.2 mol) of diethyl 4-propylcyclohexylmalonate dropwise for 30 minutes, after which it was stirred for 5 hours on a hot water bath at 80°-90° C. The reactant was cooled to room temperature, and 50 cm3 of water and 1,000 cm3 of 15% HCl were dropped while stirring. The oily layer was removed, and the water layer was extracted with toluene and combined with the oily layer and washed with 10% HC1 and water. The toluene was removed, and the residue was recrystallized from hexane to obtain 18 g (0.09 mol) of 2-(4'-propylcyclohexyl)propane-1,3-diol (trans-cis form mixture).

Workup

  1. stirringwhile stirring
  2. customThe oily layer was removed
  3. extractionthe water layer was extracted with toluene
  4. washwashed with 10% HC1 and water
  5. customThe toluene was removed
  6. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-8744d70ebe2a48a59bc132982550a670
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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