Hydrochloric Acid → HCID 19603829, compound

HRID 1604646Notes

Reaction equation

HRID 1604646 reaction equation
[CH:1]([C:3]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:4]=1[O:5][CH:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:2].[BH4-].[Na+].Cl>O1CCCC1.O.O>[OH:2][CH2:1][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:4]=1[O:5][CH:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18351607HCID 18351607, compound

Product 1

HCID 19603829HCID 19603829, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution ethyl 2-(2-formyl-6-methoxyphenoxy)propionate (2.60 g) in tetrahydrofuran-water (9:1) was ice-cooled and sodium borohydride (185 mg) was added. The mixture was stirred at the same temperature for two hours. Diluted hydrochloric acid (1N, 5 ml) was added to the solution and the mixture was stirred for an hour. The mixture was diluted with water and was extracted with ethyl acetate. The organic layer was separated and washed with brine and dried over magnesium sulfate. After concentration, the crude product was purified on a column of silica gel (29 g) eluting with a mixed solvent of toluene and ethyl acetate (7:1) to give ethyl 2-(2-hydroxymethyl-6-methoxyphenoxy)propionate (1.85 g).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred for an hour
  3. extractionwas extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter concentration
  8. customthe crude product was purified on a column of silica gel (29 g)
  9. washeluting with a mixed solvent of toluene and ethyl acetate (7:1)

Sources & evidence

ORD record
ord-e0902d5028b34a8f813cff0cd4d8aac8
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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