Hydrochloric Acid → HCID 5311925, compound

HRID 431712Notes

Reaction equation

HRID 431712 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15](C(OCC)=O)[C:16]([O:18]CC)=[O:17])=[C:11]([N+:26]([O-:28])=[O:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCO.[OH-].[Na+].Cl>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[C:11]([N+:26]([O-:28])=[O:27])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 13996347HCID 13996347, compound

Product 1

HCID 5311925HCID 5311925, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a round-bottom flask containing diethyl 2-(4-benzyloxy-2-nitrophenyl) malonate (4c) (2.00 g, 5.17 mmol) was added EtOH (45 mL) and 10% NaOH (60 mL) producing a dark brown solution. The solution was refluxed for 3 h and checked by TLC (CHCl3), at which time the solution was slightly yellowish and clear. The EtOH was removed under reduced pressure to form a yellow suspension and sufficient THF (30 mL) was added to produce a clear yellow solution which was placed in an ice bath and stirred. 6M HCl (30 mL) was slowly added to the solution to reach pH 1. The light orange solution was refluxed for another hour, at which time two layers formed. The top THF layer was collected, and the aqueous solution was extracted with CHCl3 (100 mL). The organic layers were combined and dried with anhydrous sodium sulfate. The solution was then filtered, and the filtrate was concentrated to produce 4-benzyloxy-2-nitrophenylacetic acid as an orange solid. The solid was then placed on a high vacuum and dried (1.41 g, 4.91 mmol, 95%). Mp 145-152° C.; TLC (CHCl3) Rf=0.15; 1H-NMR (CDCl3, 300 MHz) 7.76 (d, 2.7, 1H), 7.41 (m, 5H), 7.26 (d, 8.7, 1H), 7.21 (dd, 2.7, 8.7, 1H), 5.13 (s, 2H), 4.00 (s, 2H); IR (CHCl3 cast) 3400-2600 (br), 3100, 1698, 1601, 1526, 1523, 1453, 1376, 1349, 1240, 1180, 1022, 848, 815, 760, 712; EI-MS m/z (relative intensity) 287 (M+, 10). Accurate mass (EI-MS) for C15H13NO5: calcd. 287.0794, obsd. 287.0799.

Workup

  1. customproducing a dark brown solution
  2. temperatureThe solution was refluxed for 3 h
  3. customThe EtOH was removed under reduced pressure
  4. customto form a yellow suspension and sufficient THF (30 mL)
  5. additionwas added
  6. customto produce a clear yellow solution which
  7. customwas placed in an ice bath
  8. temperatureThe light orange solution was refluxed for another hour, at which time two layers
  9. customformed
  10. customThe top THF layer was collected
  11. extractionthe aqueous solution was extracted with CHCl3 (100 mL)
  12. dry with materialdried with anhydrous sodium sulfate
  13. filtrationThe solution was then filtered
  14. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bac62d33bb354e7f8cecdee4a7016d9c
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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