Sodium Methoxide → Ethyl (4-hydroxy-2-methylphenoxy)acetate

HRID 445858Notes

Reaction equation

HRID 445858 reaction equation
C([O:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([CH3:18])[CH:6]=1)(=O)C.C[O-].[Na+]>CO>[OH:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([CH3:18])[CH:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21986316Ethyl 2-(4-acetoxy-2-methylphenoxy)acetate

Product 1

HCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(4-acetoxy-2-methylphenoxy)acetate (684) (6.79 g, 27 mmol) in dry methanol (150 mL) was added sodium methoxide (1.1 eq.) and the reaction was stirred at room temperature under N2 for 3 hours. The reaction was quenched with 1M HCl and the volatiles were removed in vacuo. The oil was dissolved in ethyl acetate (100 mL) and washed with water (2×100 mL), and brine (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afforded ethyl 2-(4-hydroxy-2-methylphenoxy)acetate (685) as a white solid (77%).

Workup

  1. customThe reaction was quenched with 1M HCl
  2. customthe volatiles were removed in vacuo
  3. dissolutionThe oil was dissolved in ethyl acetate (100 mL)
  4. washwashed with water (2×100 mL), and brine (100 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7eff18d0ee7a472aa2afc3aacf639a7b
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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