Trifluoroacetic acid → HCID 57852675, compound

HRID 657467Notes

Reaction equation

HRID 657467 reaction equation
[N+:1]([C:4]1[CH:44]=[CH:43][CH:42]=[CH:41][C:5]=1[CH2:6][O:7][C:8](=[O:40])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[C:22]([C:33]([O:35]C(C)(C)C)=[O:34])[CH:23]=[C:24]([CH:32]=1)[C:25]([O:27]C(C)(C)C)=[O:26])([O-:3])=[O:2].FC(F)(F)C(O)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:44]=[CH:43][CH:42]=[CH:41][C:5]=1[CH2:6][O:7][C:8](=[O:40])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:32]=[C:24]([C:25]([OH:27])=[O:26])[CH:23]=[C:22]([CH:21]=1)[C:33]([OH:35])=[O:34])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57852677HCID 57852677, compound

Product 1

HCID 57852675HCID 57852675, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The previously prepared compound, di-tert-butyl 5-(11-(2-nitrobenzyloxy)-11-oxoundecyloxy)isophthalate, was dissolved in CH2Cl2 (10 mL) producing a yellow solution. Trifluoroacetic acid (TFA) (10 mL) was slowly added while stirring. The solution was stirred at room temperature for 1 hour. The solvent was removed by rotovap producing a white solid, which was washed four times with CH2Cl2 and dried under vacuum. A white power was produced. Yield: 0.127 g (100%). 1H-NMR (DMSO-d6) δ (ppm): 13.3 (s, 2H, OH), 8.1 (d, 1H, Ar), 8.0 (s, 1H, Ar), 7.8 (t, 1H, Ar), 7.7 (d, 1H, Ar), 7.6 (t, 11H, Ar), 7.6 (s, 2H, Ar), 5.4 (s, 2H, O—CH2), 4.0 (t, 2H, CH2—O), 2.4 (t, 2H, CH2—C═O), 1.7 (m, 2H, CH2), 1.5 (m, 2H, CH2), 1.4 (m, 2H, CH2), 1.2 (m, 10H, CH2). 13C-NMR (DMSO-d6) δ (ppm): 172.8, 166.7, 159.1, 147.8, 134.4, 132.9, 131.8, 129.9, 129.7, 125.2, 122.4, 119.3, 68.4, 62.6, 33.6, 29.2, 29.1, 29.0, 28.9, 28.8, 28.7, 25.7, 24.7. MS (ESI): (M)=500.4 (calc. 501.53).

Workup

  1. customproducing a yellow solution
  2. stirringThe solution was stirred at room temperature for 1 hour
  3. customThe solvent was removed by rotovap
  4. customproducing a white solid, which
  5. washwas washed four times with CH2Cl2
  6. customdried under vacuum
  7. customA white power was produced

Sources & evidence

ORD record
ord-fb43c93d5914456da4a212565db20807
Source dataset
uspto-grants-2011_12
Patent number
US08076125B2

Reaction notes

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