Tetrabutylammonium Fluoride → Methyl 2-(3-hydroxyphenoxy)acetate

HRID 1051105Notes

Reaction equation

HRID 1051105 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:28]=[C:29]([CH:36]=[CH:37][CH:38]=1)[O:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])(C(C)(C)C)(C)C>C1COCC1>[OH:26][C:27]1[CH:28]=[C:29]([CH:36]=[CH:37][CH:38]=1)[O:30][CH2:31][C:32]([O:34][CH3:35])=[O:33]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 125464147Methyl 2-(3-((t-butyldimethylsilyl)oxy)phenoxy)acetate

Product 1

HCID 10261746Methyl 2-(3-hydroxyphenoxy)acetateYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride in THF (1 M, 3.4 mL, 3.4 mmol) was added to a solution of methyl 2-(3-((t-butyldimethylsilyl)oxy)phenoxy)acetate (0.50 g, 1.7 mmol) in THF (5 mL) in a 100 mL round bottom flask. The reaction was allowed to stir overnight at room temperature. The reaction was quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (200 mL). The organic extract was dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (40 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 0.19 g (60%) of methyl 2-(3-hydroxyphenoxy)acetate.

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride (100 mL)
  2. extractionextracted with ethyl acetate (200 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude residue was purified by combiflash (40 g column, hexanes→100% ethyl acetate/hexanes, gradient)

Sources & evidence

ORD record
ord-0510814b9010490fbfb2fe2eb94a51e4
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

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