Hydrochloric Acid → Methyl 2-(4-hydroxyphenoxy)acetate

HRID 408671

Reaction equation

HRID 408671 reaction equation
C([O:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)(=O)C.C[O-].[Na+].Cl>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 20717764Methyl (4-acetoxy-phenoxy)-acetate

Product 1

HCID 602731Methyl 2-(4-hydroxyphenoxy)acetateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 100 ml round flask were added 1.512 g methyl (4-acetoxy-phenoxy)-acetate dissolved in 50 ml anhydrous methanol, 0.364 g sodium methoxide. The mixture was stirred at room temperature for 1 hour. To the stirred mixture was added dilute HCl to adjust pH to weak acidity. The solvent was removed by evaporation. To the residue was added water. The solution was extracted with ethyl acetate for three times. The extract was dried, filtrated and evaporated to obtain 1.004 g of a brown solid, yield 85%. 1H-NMR (400 MHz, DMSO-d6, δ ppm) δ 3.679 (3H, s), 4.646 (2H, s), 6.672 (2H, d), 6.754 (2H, d), 9.0 (1H, s).

Workup

  1. customThe solvent was removed by evaporation
  2. additionTo the residue was added water
  3. extractionThe solution was extracted with ethyl acetate for three times
  4. customThe extract was dried
  5. filtrationfiltrated
  6. customevaporated

Sources & evidence

ORD record
ord-c36ed3d2892942d79344c5d41152f084
Source dataset
uspto-grants-2014_06
Patent number
US08759355B2

Linked notes

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