Sodium Hydroxide → HCID 86585343, compound

HRID 2187257Notes

Reaction equation

HRID 2187257 reaction equation
Cl[CH2:2][CH:3]([OH:16])[CH2:4][O:5][C:6]1([CH3:15])[CH2:11][CH2:10][CH:9]([CH:12]([CH3:14])[CH3:13])[CH2:8][CH2:7]1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C1(C)C=CC=CC=1>[O:16]1[CH:3]([CH2:4][O:5][C:6]2([CH3:15])[CH2:11][CH2:10][CH:9]([CH:12]([CH3:14])[CH3:13])[CH2:8][CH2:7]2)[CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69824763HCID 69824763, compound

Product 1

HCID 86585343HCID 86585343, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, into a reaction flask (volume: 200 ml) were added 1-chloro-3-1-menthoxypropan-2-ol (50 g, chemical purity: 97.8%, 0.1968 mol) obtained in Example 1, toluene (75 ml), a 50% aqueous sodium hydroxide solution (31.49 g, 0.3936 mol) and a 50% aqueous benzyltrimethylammonium chloride solution (1.46 g, 4.26 mmol), and they were reacted at 75° C. for 2 hours. After completion of the reaction, the organic layer was washed with water and then the solvent (toluene) was removed to obtain an oily substance. The oily substance was distilled under reduced pressure to obtain 1,2-epoxy-3-1-menthoxypropane (34.6 g, chemical purity: 98.25%) [boiling point: 75-80° C./10.7 Pa (0.08 mmHg)] as a colorless transparent oily substance (yield: 97.0% based on 1-chloro-3-1-menthoxypropan-2-ol).

Workup

  1. customAfter completion of the reaction
  2. washthe organic layer was washed with water
  3. customthe solvent (toluene) was removed
  4. customto obtain an oily substance
  5. distillationThe oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-b36695b2771e4d908f6fb251b15f1b5c
Source dataset
uspto-grants-2002_06
Patent number
US06407293B1

Reaction notes

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