Ethylene Glycol → HCID 22615139, compound

HRID 852408Notes

Reaction equation

HRID 852408 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[F:12])=[O:3].[CH2:13](O)[CH2:14][OH:15]>C1(C)C=CC=CC=1.CCOCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[C:2]1([CH3:1])[O:15][CH2:14][CH2:13][O:3]1

Participants

6

Reactant 2

HCID 174Ethylene Glycol2×HCID 5928212'-Fluoro-4'-methoxyacetophenone

Product 1

HCID 22615139HCID 22615139, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst2×HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 5.00 g (30.00 mmol) 2-fluoro-4-methoxyacetophenone, 1.11 ml (33.00 mmol) ethylene glycol and 0.28 g (1.49 mmol) p-toluene sulfonic acid hydrate in 50 ml toluene was refluxed in a Dean-Stark apparatus for 2.5 days. After 0.5 and 1.5 days additional 1.11 ml (33.00 mmol) ethylene glycol and 0.28 g (1.49 mmol) p-toluene sulfonic acid hydrate were added. After cooling, the reaction was diluted in ether and washed with aqueous saturated NaHCO3 (two times) and aqueous 10% NaCl solution. The water phases were extracted with ether, the organic phase was dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography (SiO2; n-heptane/AcOEt=95:5) to give 4.90 g of the title compound as brown liquid (with ca 10% of starting material, seen in 1H-NMR).

Workup

  1. temperatureAfter cooling
  2. washwashed with aqueous saturated NaHCO3 (two times) and aqueous 10% NaCl solution
  3. extractionThe water phases were extracted with ether
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (SiO2; n-heptane/AcOEt=95:5)

Sources & evidence

ORD record
ord-4122e60cf4d6492eb81154f50afc2284
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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