Hydrochloric Acid → Ethyl alpha-(hydroxymethylene)-4-methoxyphenylacetate

HRID 133182

Reaction equation

HRID 133182 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.[H-].[Na+].Cl.[CH:18](OCC)=[O:19]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[CH:18][OH:19])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 84174Ethyl 4-methoxyphenylacetate

Product 1

HCID 67418551Ethyl alpha-(hydroxymethylene)-4-methoxyphenylacetate

Procedure

8.9 ml of ethyl p-methoxyphenylacetate are dissolved in 80 ml of ethyl formate. 4.6 g of 50% NaH are added portionwise and then the mixture is stirred at ambient temperature for 12 hours. It is poured onto a 1N HCl solution and then extraction is carried out with AcOEt. Purification is carried out by chromatography on a silica column eluted with an AcOEt/heptane (05/95; v/v) mixture to produce 4.0 g of the expected compound in the liquid form.

Workup

  1. extractionextraction
  2. customPurification
  3. washeluted with an AcOEt/heptane (05/95; v/v) mixture

Sources & evidence

ORD record
ord-ed1232b3a26c47d492e3e6672f4cbf4a
Source dataset
uspto-grants-2008_06
Patent number
US07390818B2

Linked notes

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