Sodium Hydroxide → HCID 178444361, compound

HRID 1032876Notes

Reaction equation

[CH2:1]1[O:3][C@H:2]1[CH2:4]Cl.[CH2:6]([C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)[CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:6]([C@H:11]1[CH2:12][CH2:13][C@H:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:4][C@H:2]3[O:3][CH2:1]3)=[CH:21][CH:22]=2)[CH2:15][CH2:16]1)[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of the above R-(-)-epichlorohydrin (5.55 g), 4(trans-4-n-pentylcyclohexyl)phenol (2.46 g) of the following formula: ##STR15## and benzyltriethylammonium chloride (0.04 g) is added dropwise aqueous sodium hydroxide (NaOH 0.45 g, water 15 ml) with stirring at 60° C. over a period of 20 minutes, and the mixture is further refluxed for one hour. The reaction mixture is cooled to room temperature and extracted twice with ether. The extract is washed once with a saturated saline solution and distilled under reduced pressure to remove the solvent. The reside is purified by silica gel chromatography to give (S)-2,3-epoxypropyl 4-(trans-4-n-pentylcyclohexyl)phenyl ether (1.8 g) of the following formula: ##STR16##

Workup

temperaturethe mixture is further refluxed for one hour
temperatureThe reaction mixture is cooled to room temperature
extractionextracted twice with ether
washThe extract is washed once with a saturated saline solution
distillationdistilled under reduced pressure
customto remove the solvent
customThe reside is purified by silica gel chromatography

Sources & evidence

ORD record: ord-568c23eb397f408aa611c1667139c5bf
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05308540

Reaction notes

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