Sodium Hydroxide → HCID 178444361, compound

HRID 1165400Notes

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 residue 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 residue is purified by silica gel chromatography

Sources & evidence

ORD record: ord-d6e52ba47c3940aeacd98322e5d684b3
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04909957

Reaction notes

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