Hydrochloric Acid → Methyl 2-(2-hydroxy-methyl-5-methylphenoxy)propionate

HRID 482385Notes

Reaction equation

HRID 482385 reaction equation
C([C:3]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:4]=1[O:5][CH:6]([CH3:11])[C:7]([O:9][CH3:10])=[O:8])=O.[BH4-].[Na+].Cl.[CH3:20][OH:21]>C[O-].[Na+]>[OH:21][C:20]1[C:15]([CH3:3])=[CH:14][C:13]([CH3:16])=[CH:12][C:4]=1[O:5][CH:6]([CH3:11])[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 4311764Sodium borohydrideHCID 23286419Methyl 2-(formyl-5-methylphenoxy)propionate

Product 1

HCID 18981070Methyl 2-(2-hydroxy-methyl-5-methylphenoxy)propionate

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideCatalyst

Procedure

To a solution of 7.89 g (0.0355 mole) of methyl 2-(2-formyl-5-methyl-phenoxy)propionate in 20 mL of methanol, cooled to 5° C., was added a solution of 0.10 g (0.0018 mole) of sodium methoxide in 20 mL of methanol. While the temperature was maintained between 0° C. and 5° C., 0.36 g (0.0094 mole) of sodium borohydride was added to the reaction during a period of about 10 minutes. The reaction mixture was allowed to warm to ambient temperature, where it was stirred for two hours. At the end of this period, the reaction mixture was poured into 75 mL of 0.25N hydrochloric acid. This mixture was extracted twice with methylene chloride. The combined extracts were washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure, leaving a colorless oil as a residue. This oil was placed on a silica gel column and eluted first with methylene chloride/ethyl acetate (95/5) and then with the same solvents (90/10). After the product-containing fractions were combined and the solvents evaporated under reduced pressure, 5.76 g of methyl 2-(2-hydroxy-methyl-5-methylphenoxy)propionate was isolated as a colorless oil. The NMR and IR spectra were consistent with the proposed structure.

Workup

  1. temperatureWhile the temperature was maintained between 0° C. and 5° C.
  2. extractionThis mixture was extracted twice with methylene chloride
  3. washThe combined extracts were washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customleaving a colorless oil as a residue
  8. washeluted first with methylene chloride/ethyl acetate (95/5)
  9. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-ae314619f9b04fe4baeea65a84a28972
Source dataset
uspto-grants-1998_08
Patent number
US05798316

Reaction notes

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