Ammonium formate → Methyl 4-hydroxyphenyllactate

HRID 400131Notes

Reaction equation

HRID 400131 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([OH:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:21][CH:16]([CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10493427Methyl 3-[4-(benzyloxy)phenyl]-2-hydroxypropanoate

Product 1

HCID 170975Methyl 4-hydroxyphenyllactate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of methyl 3-(4-benzyloxyphenyl)-2-hydroxypropanoate (c.f. International Patent Appl. Publication No. WO9101337) (5.72 g) in methanol (120 mL) was added to an ice cooled suspension of 10% Palladium charcoal (1.90 g) in methanol (30 mL) under a nitrogen atmosphere. Solid ammonium formate (6.4 g) was added and the mixture heated at reflux for 15 minutes, then allowed to cool to room temperature. The catalyst was removed by filtering the reaction mixture through diatomaceous earth and the solvent evaporated. The residue was suspended in dilute hydrochloric acid (2M, 100 mL) and extracted with ethyl acetate (2×400 mL). The combined ethyl acetate solutions were washed with water (400 mL), brine (400 mL), dried (MgSO4) and evaporated. The resulting gum was chromatographed on silica gel with 1.5% methanol in dichloromethane as eluent to afford the title compound, mp 42°-43° C.

Workup

  1. temperaturecooled
  2. temperaturethe mixture heated
  3. temperatureat reflux for 15 minutes
  4. customThe catalyst was removed
  5. filtrationby filtering the reaction mixture through diatomaceous earth
  6. customthe solvent evaporated
  7. extractionextracted with ethyl acetate (2×400 mL)
  8. washThe combined ethyl acetate solutions were washed with water (400 mL), brine (400 mL)
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customThe resulting gum was chromatographed on silica gel with 1.5% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-da56e3f7b74642f59c8cb536f72ccb14
Source dataset
uspto-grants-1998_10
Patent number
US05827865

Reaction notes

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