Dimethyl Sulfide → (Z)-6-((4-methoxybenzyl)oxy)-4-methylhex-4-enal

HRID 1160567Notes

Reaction equation

HRID 1160567 reaction equation
[CH3:1]/[C:2](/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:3]/[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[O:21]=[O+][O-].CSC>ClCCl.N1C=CC=CC=1>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][O:5][CH2:4]/[CH:3]=[C:2](/[CH3:1])\[CH2:15][CH2:16][CH:17]=[O:21])=[CH:12][CH:11]=1.[CH3:1]/[C:2](/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:3]/[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 594447481-({[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}methyl)-4-methoxybenzene

Product 2

HCID 16732373(Z)-6-((4-methoxybenzyl)oxy)-4-methylhex-4-enalHCID 594447481-({[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}methyl)-4-methoxybenzene

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

1-({[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}methyl)-4-methoxybenzene (75.0 g, 273 mmol) was dissolved in dichloromethane (1.13 l) and pyridine (11.3 ml). This reaction solution was cooled to −78° C., to which ozone was bubbled (flow rate 2 l/min, electric voltage 90 V) for 170 minutes with stirring. After addition of dimethylsulfide (80.3 ml, 1.09 mol), the reaction solution was allowed to warm to room temperature and was stirred overnight. The reaction solution was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=4:1) and the title compound (36.9 g) was obtained as a colorless oil while 1-({[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}methyl)-4-methoxybenzene (14.1 g) was recovered.

Workup

  1. customwas bubbled (flow rate 2 l/min, electric voltage 90 V) for 170 minutes
  2. stirringwas stirred overnight
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-87a208cccdea4e26b0524b7f24ed929d
Source dataset
uspto-grants-2010_10
Patent number
US07816401B2

Reaction notes

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