t-Butyl 3-nitrobenzyloxyacetate → 3-Nitrobenzyloxyacetic acid

HRID 260316Notes

Reaction equation

HRID 260316 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][O:8][CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])([O-:3])=[O:2]>C(O)=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][O:8][CH2:9][C:10]([OH:12])=[O:11])([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 22401159t-Butyl 3-nitrobenzyloxyacetate

Product 1

HCID 224011503-Nitrobenzyloxyacetic acidYield 98.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

t-Butyl 3-nitrobenzyloxyacetate (5 g, 18.7 mM) was dissolved in formic acid (50 ml) and stirred at ambient temperature for 48 hours. Solvents were removed to give 3-nitrobenzyloxyacetic acid (3.9 g, 98%). NMR (DMSO-d6): δ4.15 (s, 2H); 4.69 (s, 2H); 7.66 (t, 1H); 7.81 (d, 1H); 8.13-8.22 (m, 2H); 12.73 (br, 1H).

Workup

  1. customSolvents were removed

Sources & evidence

ORD record
ord-655b5de6cdff410fa4333ad5199add6d
Source dataset
uspto-grants-1996_06
Patent number
US05527791

Reaction notes

Loading…