Hydrochloric Acid → 3-iso-Pentyloxy-5-nitrobenzoic acid

HRID 2266940Notes

Reaction equation

HRID 2266940 reaction equation
O[Li].O.[CH2:4]([O:9][C:10]1[CH:11]=[C:12]([CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[C:13]([O:15]CCC(C)C)=[O:14])[CH2:5][CH:6]([CH3:8])[CH3:7].Cl>O.CO.C1COCC1>[CH2:4]([O:9][C:10]1[CH:11]=[C:12]([CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[C:13]([OH:15])=[O:14])[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58060846iso-Pentyl 3-iso-pentyloxy-5-nitrobenzoate

Product 1

HCID 580608373-iso-Pentyloxy-5-nitrobenzoic acidYield 96.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4.05 g (96.6 mmol) LiOH.H2O were dissolved in a mixture of 100 mL H2O, 30 mL methanol and 40 mL THF. 5.2 g (16 mmol) 9 were added and it was stirred at r.t. for 20 h, during this time turning into a yellow, homogeneous solution. Most of the THF and methanol were taken off by rotovapping, the remaining solution was acidified with 2 N HCl and extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried with MgSO4 and put under vacuum, yielding 3.9 g (96%) of a yellow solid, which was pure by NMR. For characterization, a sample was recrystallized from ethyl acetate. mp 142° C.; 1H NMR (CDCl3) δ 8.53 (dd, J1=1.5 Hz, J2=2.4 Hz, 1H), 7.98 (t, J1=2.4 Hz, J2=2.4 Hz, 1H), 7.94 (dd, J1=1.5 Hz, J2=2.4 Hz, 1H), 4.14 (t, J=6.4 Hz, 2H, PhOCH2CH2CH(CH3)2), 1.99-1.80 (m, 1H), 1.80-1.70 (m, 2H), 1.01 (d, J=6.3 Hz, 6H, CH(CH3)2); 13C NMR (acetone-d6) 165.52, 160.75, 150.12, 133.90, 122.35, 116.67, 113.68, 68.41, 38.33, 25.68, 22.74; ESI-MS m/z 252 [M−1]+.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-e8900efcf8df46be9f599c15c1060722
Source dataset
uspto-grants-2010_12
Patent number
US07858737B2

Reaction notes

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