Sodium Hydroxide → 3-(4-Hydroxyphenyl)-2-methoxypropanoic acid

HRID 1353201Notes

Reaction equation

HRID 1353201 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([O:14][CH3:15])[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([O:14][CH3:15])[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10965756Methyl 3-(4-hydroxyphenyl)-2-methoxypropanoate

Product 1

HCID 112410113-(4-Hydroxyphenyl)-2-methoxypropanoic acidYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(4-hydroxyphenyl)-2-methoxypropanoate (132 g, 0.631 mol) was dissolved in methanol (700 mL) and 5N sodium hydroxide (631 mL, 3.16 mol) was added dropwise at ambient temperature. The solution was stirred for 16 h at ambient temperature. The methanol was removed under vacuum, and water (500 mL) was added. The mixture was extracted with MTBE (2×500 mL). The aqueous solution was brought to pH=1 with concentrated HCl and then extracted with MTBE (2×500 nL). The organic extracts were dried (MgSO4), filtered, and concentrated under vacuum to give racemic 3-(4-hydroxyphenyl)-2-methoxypropanoic acid as an oil (110 g), which crystallized upon standing. 1H-NMR (DMSO): 7.0 (d, 2H); 6.6 (d, 2H); 4.0 (m, 1H); 2.8 (m, 2H); MS (ES−) m/z 195.1 (M−1).

Workup

  1. customThe methanol was removed under vacuum, and water (500 mL)
  2. additionwas added
  3. extractionThe mixture was extracted with MTBE (2×500 mL)
  4. extractionextracted with MTBE (2×500 nL)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f41b3661c35b447db6d6981b8beeeb5b
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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