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

HRID 1876416Notes

Reaction equation

HRID 1876416 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-c1175720ea8b41dc9709de5a936fdf81
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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