1,2-Dimethoxyethane → HCID 21427644, compound

HRID 437988Notes

Reaction equation

[H-].[Na+].C(COC)OC.COP([CH2:15][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])(=O)OC.[C:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1[CH:35]=O)([O:25][CH3:26])=[O:24]>C(O)(=O)C>[C:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1/[CH:35]=[CH:15]/[C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([O:25][CH3:26])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.25 g. of this benzyl alcohol in 75 ml. of chloroform is added to a slurry of 12.5 g. of activated manganese dioxide in 75 ml. of chloroform. The mixture is stirred for one hour, filtered and the solvent is evaporated to leave 2-(6-carbomethoxyhexyl)benzaldehyde as a clear oil. To a slurry of 260 ml. of a dispersion of sodium hydride in mineral oil in 40 ml. of dimethoxyethane is added a solution of 1.31 g. of dimethyl(2-oxoheptyl)phosphonate in 25 ml. of dimethoxyethane. The slurry is stirred for one hour, cooled to 0° C. and 1.22 g. of the benzaldehyde in 20 ml. of dimethoxyethane is added. The mixture is stirred at 0° for 30 minutes and at room temperature for three hours. It is then neutralized with acetic acid and the solvent removed in vacuo. The residue is chromatographed on silica gel to yield 1-(6-carbomethoxyhexyl)-2-(3-oxo-trans-1-octenyl)benzene as a pale yellow oil.

Workup

stirringThe mixture is stirred at 0° for 30 minutes and at room temperature for three hours
customthe solvent removed in vacuo
customThe residue is chromatographed on silica gel

Sources & evidence

ORD record: ord-e4565da8a3c448f88c0e5e00cc2c52ff
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04032656

Reaction notes

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