Oxygen → 4-Methoxy-4-methylpentanal

HRID 2247798Notes

Reaction equation

HRID 2247798 reaction equation
[CH3:1][C:2]([O:10][CH3:11])([CH2:4][CH2:5][CH:6]=C(C)C)[CH3:3].[O:12]=[O+][O-].O=O.CSC>CO.C(Cl)Cl>[CH3:11][O:10][C:2]([CH3:3])([CH3:1])[CH2:4][CH2:5][CH:6]=[O:12]

Participants

7

Reactant 4

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 24823OzoneHCID 147939932,6-Dimethyl-2-methoxyhept-5-ene

Product 1

HCID 118294744-Methoxy-4-methylpentanal

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred, cooled (-65~C.) mixture of 2,6-dimethyl-2-methoxyhept-5-ene (125 g, 1.25 mol), methylene chloride (500 mL) and methanol (500 mL) was treated with a gas stream enriched with ozone. Upon the appearance of a blue color pure oxygen was passed through the mixture followed by nitrogen. Dimethyl sulfide (88 mL, 1.4 mol) was added and the mixture was allowed to stand 16 hours at 25~C. Upon workup 4-methoxy-4-methylpentanal was obtained, bp30 85-87~C. (64.4 g); NMR(CDCl3) 1.2(s,6H), 1.9(t,2H), 2.5(m,2H), 3.2(s,3H), 9.8(t,1H); IR(neat) 2975, 2825, 2725, 1730, 1470, 1370, 1090 cm-1 ;MS(m/e) 43, 73, 83, 115. ##STR37##

Workup

  1. temperatureA stirred, cooled
  2. additionwas treated with a gas stream

Sources & evidence

ORD record
ord-b9c19fc45fb344b6a5b0bb3ee2d8291c
Source dataset
uspto-grants-1991_08
Patent number
US05037802

Reaction notes

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