Acetic Acid → HCID 21435241, compound

HRID 2398437Notes

Reaction equation

[CH3:1][C:2]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[CH:6][C:5]=1[OH:14])=[O:3].O1CCOCC1.[H-].[Na+].C(O)(=O)C.C([O:29][C:30](=O)[C:31]([CH3:35])([CH3:34])[C:32]#[N:33])C>>[CH3:34][C:31]([CH3:35])([C:30](=[O:29])[CH2:1][C:2](=[O:3])[C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[CH:6][C:5]=1[OH:14])[C:32]#[N:33]

Participants

Reactant 5

HCID 176Acetic Acid

HCID 24758Sodium hydride

HCID 312751,4-Dioxane

HCID 66654Xanthoxylin

HCID 344887Ethyl 2-Cyano-2-methylpropionate2×

Product 1

HCID 21435241HCID 21435241, compound

Procedure

A mixture of 73.5 g of 2-hydroxy-4,6-dimethoxyacetophenone, 260 g of dimethylcyanoacetic acid ethyl ester and 375 ml of absolute dioxane is introduced into a suspension of 28.6 g of NaH in 7.3 g of dimethylcyanoacetic acid ethyl ester at 0°-10°, while stirring. The mixture is heated for 1 hour at 80°, cooled and poured into acetic acid and the resulting solution is stirred into ice water to give 2,2-dimethyl-3,5-dioxo-5-(2-hydroxy-4,6-dimethoxyphenyl)-pentanonitrile; m.p. 112°-113°.

Workup

temperatureThe mixture is heated for 1 hour at 80°
temperaturecooled

Sources & evidence

ORD record: ord-1bd55e5243c241fab087d9c6e5896330
Source dataset: uspto-grants-1977_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04024272

Reaction notes

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