Water → 2-Ethoxy-3-(4-hydroxy-2-nitrophenyl)propanoic acid methyl ester

HRID 987266Notes

Reaction equation

HRID 987266 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]([O:23][CH2:24][CH3:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[CH:8][C:7]=1[N+:20]([O-:22])=[O:21].CSC.B(F)(F)F.CCOCC.O>ClCCl>[CH3:1][O:2][C:3](=[O:26])[CH:4]([O:23][CH2:24][CH3:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[N+:20]([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 538566552-Ethoxy-3-(4-benzyloxy-2-nitrophenyl)propanoic acid methyl ester

Product 1

HCID 538988402-Ethoxy-3-(4-hydroxy-2-nitrophenyl)propanoic acid methyl esterYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Ethoxy-3-(4-benzyloxy-2-nitrophenyl)propanoic acid methyl ester (1.5 g; 4.06 mmole) was dissolved in dichloromethane (8 ml) and dimethylsulfide (8 ml) was added. Boron trifluoride diethyl etherate (5.0 ml; 40.6 mmole) was added under stirring. The reaction mixture was stirred at room temperature for 4 hours and then poured into water and more dichloromethane was added. The phases were separated and the organic phase was washed with water and brine and dried with magnesium sulfate. Evaporation to remove the solvent gave 1.04 g (95% yield) of 2-ethoxy-3-(4-hydroxy-2-nitrophenyl)propanoic acid methyl ester.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 hours
  2. additionwas added
  3. customThe phases were separated
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried with magnesium sulfate
  6. customEvaporation
  7. customto remove the solvent

Sources & evidence

ORD record
ord-61bb798f6fec47ba9c11000f3914bff2
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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