Water → Ethyl 3-(2-methoxyphenyl)-3-(2-methoxymethoxy-3-methylphenyl)propenoate

HRID 359193Notes

Reaction equation

HRID 359193 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])=O.[Na].[OH2:23].[CH3:24][CH2:25][O:26][CH2:27][CH3:28]>C(COC)OC>[CH3:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]([C:6]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:5]=1[O:4][CH2:3][O:2][CH3:1])=[CH:24][C:25]([O:26][CH2:27][CH3:28])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 5360545SodiumHCID 198126582-Methoxymethoxy-3-methyl-2'-methoxybenzophenone

Product 1

HCID 54221000Ethyl 3-(2-methoxyphenyl)-3-(2-methoxymethoxy-3-methylphenyl)propenoate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Methoxymethoxy-3-methyl-2'-methoxybenzophenone (17.5 g) was combined with the sodium salt of triethyl phosphonoacetate (2.2 equivalents) in 250 ml of dimethoxyethane and the mixture heated at reflux with stirring for 2 days. Water and ether were added and the organic phase was separated, extracted with water, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain an oil. This was purified by preparative liquid chromatography, eluting with a 90:10 mixture of hexane and acetone, to obtain ethyl 3-(2-methoxyphenyl)-3-(2-methoxymethoxy-3-methylphenyl)propenoate as an intermediate consisting of a mixture of isomers. The assigned structure was consistent with the proton NMR spectrum. This was dissolved in 50 ml of tetrahydrofuran and treated with 61 ml of a solution of 1 M lithium aluminum hydride in tetrahydrofuran at ambient temperature with stirring. The mixture was heated at reflux with stirring for 4 hours. It was then allowed to cool, was quenched with 10 percent sulfuric acid, and was diluted with ether. The organic phase was separated, extracted with water, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a crude product. This was purified by preparative liquid chromatography, eluting with a 95:5 mixture of hexane and acetone, to obtain 6.01 g of the title compound as a gum. The assigned structure was consistent with the proton NMR spectrum.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux
  3. customthe organic phase was separated
  4. extractionextracted with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customto obtain an oil
  9. customThis was purified by preparative liquid chromatography
  10. washeluting with a 90:10 mixture of hexane and acetone

Sources & evidence

ORD record
ord-b53e780afbd241bebb92e90f4be33922
Source dataset
uspto-grants-1991_03
Patent number
US04999448

Reaction notes

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