Ethanol → HCID 10944431, compound

HRID 546273Notes

Reaction equation

HRID 546273 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=[O:6].[CH2:14](O)[CH3:15].S(=O)(=O)(O)O.[C:22]1(C)C=CC=C[CH:23]=1>>[CH2:22]([O:12][C:1](=[O:13])[CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH2:14][CH3:15])=[O:6])[CH3:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 66643Homophthalic acid

Product 1

HCID 10944431HCID 10944431, compound

Conditions

Temperature
20 °C

Procedure

A mixture of homophthalic acid [(2-carboxyphenyl)acetic acid] (5 g, 28 mmol), ethanol (23 ml), toluene (12 ml) and concentrated sulphuric acid (0.5 ml) was heated at reflux, using a Dean-Stark apparatus to remove water formed during the reaction, for 6 hrs and then overnight. The mixture was cooled to 20° C., diluted with toluene (˜50 ml) and washed with saturated aqueous sodium hydrogen carbonate solution (˜50 ml). The aqueous layer was separated and extracted with more toluene (˜50 ml) and then the combined toluene washings were washed with saturated aqueous sodium chloride solution and then dried over magnesium sulphate and evaporated. The resulting yellow oil was purified by automated flash silica-gel column chromatography (using a Biotage SP4), eluting with 0-25% gradient of ethyl acetate in hexane (10 column volumes) and then with a 25-50% gradient of ethyl acetate in hexane (2 column volumes), to give ethyl 2-[2-(ethyloxy)-2-oxoethyl]benzoate (5.9 g) as a pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customto remove water
  4. customformed during the reaction, for 6 hrs
  5. customovernight
  6. washwashed with saturated aqueous sodium hydrogen carbonate solution (˜50 ml)
  7. customThe aqueous layer was separated
  8. extractionextracted with more toluene (˜50 ml)
  9. washthe combined toluene washings were washed with saturated aqueous sodium chloride solution
  10. dry with materialdried over magnesium sulphate
  11. customevaporated
  12. customThe resulting yellow oil was purified by automated flash silica-gel column chromatography (
  13. washeluting with 0-25% gradient of ethyl acetate in hexane (10 column volumes)

Sources & evidence

ORD record
ord-1994bde68cc84df2bbfe0cc88544e0f7
Source dataset
uspto-grants-2011_05
Patent number
US07935832B2

Reaction notes

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