Methanol → Methyl 2-hydroxy-2-(3-nitrophenyl)acetate

HRID 490927Notes

Reaction equation

HRID 490927 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)[C:3]#N.C[OH:15].CC[O:18][CH2:19]C>>[CH3:19][O:18][C:3](=[O:15])[CH:2]([OH:1])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 3283Diethyl EtherHCID 32778082-Hydroxy-2-(3-nitrophenyl)acetonitrile

Product 1

HCID 11789073Methyl 2-hydroxy-2-(3-nitrophenyl)acetateYield 76%

Conditions

Temperature
0 °C

Procedure

To a solution of α-hydroxy-3-nitrobenzeneacetonitrile (27.8 g, 156.1 mmol) in 500 mL of ether was added methanol (7.6 mL, 187.3 mmol). Hydrogen chloride gas was bubbled into the solution until it was saturated. The solution changed to a heterogeneous solution. The solution was cooled to 0° C. and filtered to collect the solid. The filtrate was extracted with methylene chloride, dried over sodium sulfate, filtered and concentrated to afford 25.0 g (76%) of 2-hydroxy-2-(3-nitrophenyl)ethanoic acid methyl ester, a compound of formula (S), as a yellow solid.

Workup

  1. customHydrogen chloride gas was bubbled into the solution until it
  2. filtrationfiltered
  3. customto collect the solid
  4. extractionThe filtrate was extracted with methylene chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-86f64b64484149c1bd0467d953ba47a2
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

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