Potassium Hydroxide → 4-Fluoro-3,5-dimethylphenol

HRID 1361069Notes

Reaction equation

HRID 1361069 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9]C(=O)C)=[CH:4][C:3]=1[CH3:13].[OH-].[K+]>O1CCOCC1>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:13]

Participants

4

Conditions

Temperature
25 °C

Procedure

To a solution of acetic acid 4-fluoro-3,5-dimethyl-phenyl ester in 10 mL dioxane was added 10 mL aqueous 5% KOH at 25° C. After being stirred for 30 min at 25° C., the reaction was quenched by the addition of 12 mL of 1M aqueous HCl. The mixture was extracted ethyl acetate (3×30 mL) and the combined organic layers were washed with brine (2×30 mL). The solution was dried over Na2SO4 before being concentrated under reduced pressure. The product was isolated by silica gel chromatography to afford the title compound 987 mg, as a light yellow oil.

Workup

  1. customthe reaction was quenched by the addition of 12 mL of 1M aqueous HCl
  2. extractionThe mixture was extracted ethyl acetate (3×30 mL)
  3. washthe combined organic layers were washed with brine (2×30 mL)
  4. dry with materialThe solution was dried over Na2SO4
  5. concentrationbefore being concentrated under reduced pressure
  6. customThe product was isolated by silica gel chromatography

Sources & evidence

ORD record
ord-7842e221e7d540bf8e94e7a6a4a1dcee
Source dataset
uspto-grants-2011_02
Patent number
US07879911B2

Reaction notes

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