Sodium Hydroxide → HCID 53673369, compound

HRID 1112232Notes

Reaction equation

HRID 1112232 reaction equation
[CH3:1][C:2]([CH:14]([CH3:21])[CH2:15][CH:16]=[C:17]([CH3:20])[CH2:18][CH3:19])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH3:13])=[CH:8][CH:7]=1.ClC1C=CC=C(C(OO)=[O:30])C=1.S([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>O.ClCCl>[O:30]1[C:17]([CH3:20])([CH2:18][CH3:19])[CH:16]1[CH2:15][CH:14]([CH3:21])[C:2]([CH3:1])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH3:13])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 70622300HCID 70622300, compound

Product 1

HCID 53673369HCID 53673369, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

10 g. of p-ethylphenyl 3,4,7-trimethyl-2,6-nonadienyl ether are dissolved in 110 ml. of dichloromethane and treated portionwise at -10° C. with 7.8 g. of 80% m-chloroperbenzoic acid. After completion of the treatment, the mixture is stirred for a further 2 hours at 0° C., shaken out with 10% sodium sulfite solution, 1-N sodium hydroxide solution and water, dried over sodium sulfate and evaporated. There is obtained pure 6,7-epoxy-1-(p-ethylphenoxy)-3,4,7-trimethyl-2-nonene; NMR (CDCl3): 7.25-6.7 ppm (AB-quartet of the four aromatic protons); 5.5 ppm (a vinyl proton at C-2); 4.52 ppm doublet of the --O--CH2 group); 2.59 ppm (quartet of the aromatic-bound --CH2 group); 2.8-2.2 ppm (multiplet of the protons at C-4 and C-6); 1.65 ppm (wide singlet of the methyl group at C-3); 1.78-0.8 ppm (complicated multiplet of 19 protons).

Workup

  1. dry with materialdried over sodium sulfate
  2. customevaporated

Sources & evidence

ORD record
ord-07a4e086ac224660bf19ce720d94adb5
Source dataset
uspto-grants-1978_10
Patent number
US04120974

Reaction notes

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