Hydrochloric Acid → 4-(5-Pentyl-1,3-dioxane-2-yl)cyclohexanecarboxylic acid

HRID 1977563Notes

Reaction equation

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

Participants

Conditions

Temperature: 7 °C

Procedure

4-(5-Pentyl-1,3-dioxane-2-yl)cyclohexanecarboxylic acid methylester 28.2 g (94.5 mmol) was added in ethanol 100 ml, and cooled to 7° C., and 2N-sodium hydroxide 70 ml was added dropwise. The mixture was heated to room temperature, and stirred for one hour, and 2N-sodium hydroxide 70 ml was added dropwise. After st g the mixture father one hour at room temperature, 2N-sodium hydroxide 50 ml was added dropwise, and the mixture was stirred further one hour at room temperature. 6N-Hydrochloric acid 65 ml was added to the reactant, and the product was extracted with diethylether. The extract was washed with water, a saturated sodium bicarbonate aqueous solution and then water, and dried over magnesium sulfate, and the solvent was distilled off. The residue 27.3 g was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=1/1), and recrystallized from a mixed solvent of heptane/ethanol =20/1 to obtain 4-(5-pentyl-1,3-dioxane-2-yl)cyclohexanecarboxylic acid 2.3 g (8.1 mmol). The yield was 8.6% from 4-(5-pentyl-1,3-dioxane-2-yl)cyclohexane carboxylic acid methylester.

Workup

temperatureThe mixture was heated to room temperature
stirringthe mixture was stirred further one hour at room temperature
extractionthe product was extracted with diethylether
washThe extract was washed with water
dry with materiala saturated sodium bicarbonate aqueous solution and then water, and dried over magnesium sulfate
distillationthe solvent was distilled off
customThe residue 27.3 g was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=1/1)
customrecrystallized from a mixed solvent of heptane/ethanol =20/1

Sources & evidence

ORD record: ord-c494352a9b3e430ebf9fc126ff1d78d6
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235355B1

Reaction notes

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