epsilon-CAPROLACTONE → 6-(4-Fluoro-3-methylbenzyloxy)hexanoic acid

HRID 885511Notes

Reaction equation

HRID 885511 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:8].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][C:11]=1[CH3:18].[OH-:19].[K+]>C1(C)C=CC=CC=1.O>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][O:1][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([OH:8])=[O:19])=[CH:12][C:11]=1[CH3:18]

Participants

6

Reactant 3

HCID 10401epsilon-CAPROLACTONEHCID 14797Potassium HydroxideHCID 27781354-(Bromomethyl)-1-fluoro-2-methylbenzene

Product 1

HCID 595125786-(4-Fluoro-3-methylbenzyloxy)hexanoic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of oxepan-2-one (0.562 g, 4.925 mmol) and 4-fluoro-3-methylbenzyl bromide (3.000 g, 14.774 mmol) in 20 mL of toluene, was added KOH (1.382 g, 24.625 mmol). The mixture was refluxed for 86 h. After cooling to room temperature, the reaction mixture was diluted with water (80 mL) and washed with ether. The aqueous layer was acidified with concentrated HCl to pH=2 and extracted with ether (50 mL×3). The combined organic extracts dried (Na2SO4), filtered, and concentrated under reduced pressure to give the title compound as colorless oil which was used directly in the next step without further purification (1.173 g, 94% yield). LC-MS: tR=8.0 min, m/z 277 (M+H)+.

Workup

  1. temperatureThe mixture was refluxed for 86 h
  2. washwashed with ether
  3. extractionextracted with ether (50 mL×3)
  4. dry with materialThe combined organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac8070f6620045d08ced0ce0e8c70969
Source dataset
uspto-grants-2012_08
Patent number
US08242174B2

Reaction notes

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