4-tert-Butylcyclohexanone → 2-(Bromomethyl)-8-tert-butyl-1,4-dioxaspiro[4.5]decane

HRID 1682114Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

30.15 g (120 mmol) of tin(IV) chloride were added dropwise to 115.5 g (750 mmol) of 4-tert-butylcyclohexanone in 700 ml of absolute dichloromethane at 5° C., followed by the dropwise addition of 205.5 g (1.5 mol) of epibromohydrin ##STR9## in 370 ml of absolute dichloromethane in the course of 5 hours. The mixture was stirred overnight at room temperature (20° C.), hydrolyzed with a solution of 42 g of KOH in 180 ml of water while cooling, and worked up in a conventional manner. Distillation of the crude product (279 g) under reduced pressure gave 169 g (77.5%) of 8-tert-butyl-2-bromomethyl-1,4-dioxaspiro[4,5]decane of boiling point 110° C./0.2 mbar.

Workup

customin the course of 5 hours
distillationDistillation of the crude product (279 g) under reduced pressure

Sources & evidence

ORD record: ord-445fc8120711484c9ae5c2303713a369
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05175295

Reaction notes

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