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

HRID 362285Notes

Reaction equation

HRID 362285 reaction equation
[N+](=[C:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[CH3:17][OH:18]>C1C=CC=CC=1.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[OH:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH:3]([O:18][CH3:17])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 53837765Ethyl 2-diazo-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 18794793Ethyl 3-(4-hydroxyphenyl)-2-methoxypropanoate

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 241BenzeneSolvent2×

Procedure

A solution of ethyl 2-diazo-3-(4-hydroxyphenyl)propanoate (c.f. N. Takamura and T. Mizoguchi, Tetrahedron Lett. 1971, 4495) (8.8 g) in benzene (40 mL) was added over 30 minutes to a stirred, refluxing mixture of rhodium (II) acetate dimer (10 mg), methanol 7.9 mL) and benzene (50 mL). The mixture was heated at reflux for a further 30 minutes, then allowed to cool to room temperature overnight and washed with water (2×200 mL). The benzene solution was dried (MgSO4) and evaporated and the residual oil chromatographed twice on silica gel, firstly with 20% ethyl acetate in hexane as eluent and subsequently with 4% ethyl acetate in dichloromethane as eluent to afford the title compound as an oil.

Workup

  1. temperaturerefluxing
  2. temperatureThe mixture was heated
  3. temperatureat reflux for a further 30 minutes
  4. washwashed with water (2×200 mL)
  5. dry with materialThe benzene solution was dried (MgSO4)
  6. customevaporated
  7. customthe residual oil chromatographed twice on silica gel, firstly with 20% ethyl acetate in hexane as eluent and subsequently with 4% ethyl acetate in dichloromethane as eluent

Sources & evidence

ORD record
ord-9fc04f81ed124c1fada996f998378098
Source dataset
uspto-grants-1999_02
Patent number
US05869495

Reaction notes

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