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

HRID 1677603Notes

Reaction equation

HRID 1677603 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-00dec22767434dfb871946344b645ee4
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

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