M-Cresol → ((m-Tolyloxy)methyl)oxirane

HRID 982209Notes

Reaction equation

HRID 982209 reaction equation
[OH-].[Na+].[CH:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:10].[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl>O.C1(C)C=CC=CC=1>[C:4]1([CH3:10])[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH2:11][CH:13]2[O:15][CH2:14]2)[CH:3]=1

Participants

6

Reactant 3

HCID 342M-CresolHCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide

Product 1

HCID 98180((m-Tolyloxy)methyl)oxiraneYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 50 g (1.25 mol) of NaOH in 1200 ml H2O was added 108 g (1 mol) of m-cresol freshly distilled and at 15° C. in one lot 117ml (1.5 mol) of epichlorohydrin. The emulsion was stirred at room temperature for 16 hours in a creased flask. The product was taken up in 1000 ml of toluene and washed with 500 ml water. Distillation yielded 135.7 g=82% of product, bp 61° C. (0.05 mm).

Workup

  1. washwashed with 500 ml water
  2. distillationDistillation

Sources & evidence

ORD record
ord-6c9bd7bc83744aa3aac25513d6020dcb
Source dataset
uspto-grants-1991_02
Patent number
US04994618

Reaction notes

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