Oxygen → 4-Methoxy-4-methylpentanal

HRID 483694Notes

Reaction equation

HRID 483694 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.

Workup

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

Sources & evidence

ORD record
ord-a310b8b6d0604cf08b99fcc27f281161
Source dataset
uspto-grants-1993_07
Patent number
US05225608

Reaction notes

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