Hydrochloric Acid → Methyl 2-(5-chloro-2-hydroxymethylphenoxy)propionate

HRID 1488394Notes

Reaction equation

HRID 1488394 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([CH:18]=[O:19])=[C:9]([CH:17]=1)[O:10][CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13].[BH4-].[Na+].Cl>CO>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:18][OH:19])=[C:9]([CH:17]=1)[O:10][CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 53800060Methyl 2-(5-chloro-2-formylphenoxy)propionate

Product 1

HCID 53695259Methyl 2-(5-chloro-2-hydroxymethylphenoxy)propionateYield 54.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 0.10 g (0.018 mole) of sodium methoxide in 20 mL of methanol that had been cooled to 5° C. was added a solution of 8.0 g of methyl 2-(5-chloro-2-formylphenoxy)propionate in 20 mL of methanol. While the temperature was maintained between 0° C. and 5° C. to this mixture was added 0.50 g (0.013 mole) of sodium borohydride. This addition required 10 minutes, during which gas was evolved. The yellow solution was allowed to warm up to room temperature, where it was stirred for four hours. At the end of this period the reaction mixture was poured into 100 mL of 0.25N hydrochloric acid. This mixture was extracted with methylene chloride. The extract was 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 yellow oil as a residue. This oil was placed on a silica gel column and eluted with methylene chloride/ethyl acetate (95/5). After the product-containing fractions were combined and the solvents evaporated under reduced pressure, 4.42 g of methyl 2-(5-chloro-2-hydroxymethylphenoxy)propionate was isolated as an orange oil, which subsequently solidified, m.p. 51°-52° C.

Workup

  1. temperatureWhile the temperature was maintained between 0° C. and 5° C. to this mixture
  2. additionThis addition required 10 minutes
  3. extractionThis mixture was extracted with methylene chloride
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customleaving a yellow oil as a residue
  9. washeluted with methylene chloride/ethyl acetate (95/5)
  10. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-5631118ea7194e2c9dc485d93c776925
Source dataset
uspto-grants-1997_10
Patent number
US05674810

Reaction notes

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