2-(Tert-butoxy)ethan-1-ol → 1-(3-Chlorophenyl)-2-(2-tertbutoxyethoxy)ethanol

HRID 862501Notes

Reaction equation

CC(C)([O-])C.[K+].[C:7]([O:11][CH2:12][CH2:13][OH:14])([CH3:10])([CH3:9])[CH3:8].[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]2[CH2:24][O:23]2)[CH:19]=[CH:20][CH:21]=1>C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]([OH:23])[CH2:24][O:14][CH2:13][CH2:12][O:11][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5.1 g of potassium tert-butoxide was added to 105 ml of ethylene glycol mono-tert-butyl ether. The mixture was heated to 80° C. Thereto was dropwise added 35.0 g of 2-(3-chlorophenyl)oxirane over 1 hour. The mixture was stirred for 2 hours at the same temperature. The reaction mixture was added to a mixture of 100 ml of ice water and 100 ml of ethyl acetate. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was subjected to further distillation under reduced pressure to obtain 37.7 g of colorless oily 1-(3-chlorophenyl)-2-(2-tert-butoxyethoxy)ethanol having a boiling point of 140°-146° C./0.9 mm Hg.

Workup

customover 1 hour
customThe organic layer was separated
washwashed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed by distillation under reduced pressure
customThe residue thus obtained
distillationwas subjected to further distillation under reduced pressure

Sources & evidence

ORD record: ord-e4369e0e7c5a4266a5a911e13b67da3d
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719150

Reaction notes

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