Reaction #64658

Reaction equation

2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane

6-(cyclohexen-1-yl)-2-tert-butyl-4-methylphenol

2,4-di-tert-butyl-6-(cyclohexen-1-yl)phenol

compound ( 102 )

2,4-di-tert-butyl-6-(cyclohexen-1-yl)phenol

triethylamine

→

2-[6-(cyclohexen-1-yl)-2-tert-butyl-4-methyl-phenoxy]-5,5-dimethyl-1,3,2-dioxaphosphorinane

Yield 57.1%

Solvents

mesitylene

Conditions

Workup

1. 1
   TemperatureThe reaction mixture is then refluxed for 18 hours
2. 2
   Temperaturecooled
3. 3
   Filtrationfiltered
4. 4
   Concentrationthe filtrate is concentrated on a vacuum rotary evaporator
5. 5
   OtherCrystallization of the residue from dry acetonitrile

Procedure

4.85 g (29.0 mmol) of 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane are added drop-wise over a period of about 15 minutes to a solution of 6.6 g (27.0 mmol) of 6-(cyclohexen-1-yl)-2-tert-butyl-4-methylphenol (compound (102), Example 1) and 4.0 ml (29.0 mmol) of triethylamine in 25 ml of mesitylene (1,3,5-trimethylbenzene). The reaction mixture is then refluxed for 18 hours, cooled, filtered, and the filtrate is concentrated on a vacuum rotary evaporator. Crystallization of the residue from dry acetonitrile gives 5.8 g (57%) of 2-[6-(cyclohexen-1-yl)-2-tert-butyl-4-methyl-phenoxy]-5,5-dimethyl-1,3,2-dioxaphosphorinane, m.p. 97°-102° C. (compound (201), Table 2).

Source