Hydrochloric Acid → Methyl 2-(3-hydroxymethylphenoxy)propionate

HRID 432562Notes

Reaction equation

HRID 432562 reaction equation
C[O-].[Na+].[CH:4]([C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=1)[O:9][CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[O:5].[BH4-].[Na+].Cl>CO>[OH:5][CH2:4][C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=1)[O:9][CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 18759681Methyl 2-(3-formylphenoxy)propanoate

Product 1

HCID 18759680Methyl 2-(3-hydroxymethylphenoxy)propionateYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Into 100 ml of methanol was dissolved 52 mg of sodium methoxide; the solution was cooled to 5° C. To the solution was added 1 g of methyl 2-(3-formylphenoxy)propionate was added; after adding 55 mg of sodium borohydride below 8° C. under stirring, the mixture was stirred for 2 hours at the same temperature. The reaction solution was poured into ice-cooled 2N hydrochloric acid and the mixture was extracted twice with diethyl ether. The organic layers were combined, washed once with saturated aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure to give 0.921 g of methyl 2-[3-(hydroxymethyl)phenoxy]propionate.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 2 hours at the same temperature
  3. additionThe reaction solution was poured into ice-
  4. extractionthe mixture was extracted twice with diethyl ether
  5. washwashed once with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-328a8ed1f5e245ce831073369ab25e86
Source dataset
uspto-grants-2003_12
Patent number
US06664214B1

Reaction notes

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