Oxygen → 4-Methoxy-4-methylpentanal

HRID 329471Notes

Reaction equation

HRID 329471 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)δ1.2(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-db48de3f92a1469e990c4d70e4c0bf84
Source dataset
uspto-grants-1990_01
Patent number
US04891447

Reaction notes

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