tert-Butyl hydroperoxide → Oxiranemethanol, 3-methyl-3-(4,8,12-trimethyltridecyl)-

HRID 1885209Notes

Reaction equation

HRID 1885209 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([CH2:9][CH2:10][CH2:11][C@H:12]([CH2:14][CH2:15][CH2:16]/[C:17](=[CH:19]/[CH2:20][OH:21])/[CH3:18])[CH3:13])[CH3:8])[CH3:3].C([O:26]O)(C)(C)C.S([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>[O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5]>[O:26]1[C:17]([CH3:18])([CH2:16][CH2:15][CH2:14][CH:12]([CH3:13])[CH2:11][CH2:10][CH2:9][CH:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH:19]1[CH2:20][OH:21]

Participants

6

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 5280435Phytol

Product 1

HCID 10990611Oxiranemethanol, 3-methyl-3-(4,8,12-trimethyltridecyl)-Yield 96%

Reagents, catalysts & solvents 1

HCID 178419084HCID 178419084, compoundCatalyst

Procedure

A three-necked flask of 2-liter capacity, fitted with a stirrer, reflux-condenser and thermometer, was charged with 463.6 g (1.57 moles) of phytol, 221.8 g (1.72 moles) of a 70% (by weight) aqueous solution of t-butyl hydroperoxide and 710 mg of vanadium pentoxide and the reaction was conducted at 90° C. for 6 hours. Then, 350.4 g of a 14% (by weight) aqueous solution of sodium sulfite was added and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was transferred to a separatory funnel. The upper layer was mixed with the same volume of 1N aqueous sodium hydroxide solution and stirred at room temperature and, then, extracted with n-hexane. The extract was washed with the same volume of water 3 times and the n-hexane was distilled off to give 467.0 g (yield 96%) of 2,3-epoxy-3,7,11,15-tetramethylhexadecan-1-ol.

Workup

  1. customA three-necked flask of 2-liter capacity, fitted with a stirrer, reflux-condenser
  2. customThe reaction mixture was transferred to a separatory funnel
  3. stirringstirred at room temperature
  4. extractionextracted with n-hexane
  5. washThe extract was washed with the same volume of water 3 times
  6. distillationthe n-hexane was distilled off

Sources & evidence

ORD record
ord-47a2ec1a8be44510bbbf0cef043a0671
Source dataset
uspto-grants-1992_09
Patent number
US05143921

Reaction notes

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