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

HRID 736699Notes

Reaction equation

HRID 736699 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 20B (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 about 6 hours. After cooling, the mixture was partitioned between ethyl acetate and brine and the organic phase washed with 10% sodium hydroxide solution and water. After concentration, the residue was purified by flash chromatography using 1:5 ethyl acetate/hexane to give the title compound (2.1 g, 80%). MS (DCI): m/z 227 (M+H)+.

Workup

  1. temperatureunder reflux with a Dean-Stark apparatus for about 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 and water
  5. concentrationAfter concentration
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-36e2e637a5e54e63a989a9548a12532b
Source dataset
uspto-grants-2009_09
Patent number
US07595406B2

Reaction notes

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