M-Cresol → Azetidine, 1-(diphenylmethyl)-3-(3-methylphenoxy)-

HRID 1032089Notes

Reaction equation

HRID 1032089 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.Cl.C(N(CC)CC)C.[CH3:39][C:40]1[CH:41]=[C:42](O)[CH:43]=[CH:44][CH:45]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:13]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([O:12][C:44]3[CH:43]=[CH:42][CH:41]=[C:40]([CH3:39])[CH:45]=3)[CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

10

Reactant 6

HCID 342M-CresolHCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 15053364Azetidine, 1-(diphenylmethyl)-3-(3-methylphenoxy)-

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

A stirred mixture of 48 g (0.2 mole) of 1-diphenylmethyl-3-azetidinol and 22 g (0.22 mole) of triethylamine in 800 ml of toluene under nitrogen was cooled in a water bath while 27.5 g (0.22 mole) of methanesulfonyl chloride was added dropwise. After stirring for 20 hr, the reaction mixture was treated with 200 ml of water to dissolve the triethylamine hydrochloride. The aqueous phase was separated and the toluene phase was washed with 2×100 ml water. The toluene solution was added to a mixture of 22.8 g (0.2 mole) of 3-methylphenol (95%), 24 g (0.6 mole) of sodium hydroxide and 100 mg of tetrabutylammonium bromide in 100 ml of water and the mixture was heated at reflux and stirred vigorously for 42 hr.

Workup

  1. additionwas added dropwise
  2. customThe aqueous phase was separated
  3. washthe toluene phase was washed with 2×100 ml water
  4. temperaturethe mixture was heated
  5. temperatureat reflux
  6. stirringstirred vigorously for 42 hr

Sources & evidence

ORD record
ord-fafaf78235664ee99a02d1cd23fbf6c3
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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