Methanol → Methyl 3-(4-hydroxyphenyl)-2-methoxypropanoate

HRID 400129Notes

Reaction equation

HRID 400129 reaction equation
[N+](=[C:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5])=[N-].[CH3:16][OH:17]>CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH:3]([O:17][CH3:16])[C:4]([O:6][CH3:7])=[O:5])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 887Methanol2×HCID 54320834Methyl 2-diazo-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 10965756Methyl 3-(4-hydroxyphenyl)-2-methoxypropanoate

Reagents, catalysts & solvents 1

HCID 423677Acetic acid, rhodium salt (4:2)Catalyst

Procedure

A solution of methyl 2-diazo-3-(4-hydroxyphenyl)propanoate (cf Tetrahedron Lett., 1971, 4495) (8.58 g) in methanol (120 mL) was added over 10 minutes to a mixture of rhodium (II) acetate dimer (0.18 g) in methanol (50 mL) at room temperature under a nitrogen atmosphere. The resulting mixture was heated at reflux for 5 hrs, allowed to stand at room temperature for 15 hrs, then concentrated in vacuo. The residue was dissolved in ethyl acetate (500 mL), washed with water (3×300 mL) and brine (500 mL), dried (MgSO4) and evaporated. The resulting gum was chromatographed on silica gel with a gradient of 4% ethyl acetate to 6% ethyl acetate in dichloromethane as eluent to afford the title compound. mp 61°-3° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 5 hrs
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  5. washwashed with water (3×300 mL) and brine (500 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe resulting gum was chromatographed on silica gel with a gradient of 4% ethyl acetate to 6% ethyl acetate in dichloromethane as eluent

Sources & evidence

ORD record
ord-e6f89c9d8f3848b2ad3d7dcdd2667f28
Source dataset
uspto-grants-1998_10
Patent number
US05827865

Reaction notes

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