Ethylene Glycol → Methyl 4-(1,3-dioxolan-2-yl)-2-fluorobenzoate

HRID 1673147Notes

Reaction equation

HRID 1673147 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([CH:12]=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:14](O)[CH2:15][OH:16]>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:13]1[CH2:14][CH2:15][O:16][CH:12]1[C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 54758760Methyl 2-fluoro-4-formylbenzoate

Product 1

HCID 67353522Methyl 4-(1,3-dioxolan-2-yl)-2-fluorobenzoateYield 84.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

A solution of EXAMPLE 17B (2.0 g, 11 mmol), 1,2-ethanediol (1.0 g, 16 mmol), and p-toluenesulfonic acid monohydrate (10 mg) in benzene (10 mL) was heated under reflux with a Dean-Stark apparatus for 6 hours. After cooling, the mixture was partitioned between ethyl acetate and brine and the organic phase washed with 10% sodium hydroxide solution, water and concentrated. The residue was purified by flash chromatography on silica gel (1:5 ethyl acetate/hexane) to give 2.1 g (80%) of the title compound. MS (DCI): m/z 227 (M+H)+.

Workup

  1. temperatureunder reflux with a Dean-Stark apparatus for 6 hours
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between ethyl acetate and brine
  4. washthe organic phase washed with 10% sodium hydroxide solution, water
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (1:5 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2472f51c3b504684840b7444113ece41
Source dataset
uspto-grants-2011_08
Patent number
US07999117B2

Reaction notes

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