Potassium Carbonate → HCID 57852677, compound

HRID 657466Notes

Reaction equation

HRID 657466 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[N+:43]([O-:45])=[O:44])=[O:34].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:43]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[CH2:36][O:35][C:33](=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:1][C:2]1[CH:14]=[C:6]([C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([O-:45])=[O:44]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 45378738HCID 45378738, compoundHCID 57852678HCID 57852678, compound

Product 1

HCID 57852677HCID 57852677, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Previously prepared di-tert-butyl 5-hydroxyisophthalate (0.597 g, 2.03 mmol) and previously prepared 2-nitrobenzyl 11-bromoundecanoate (1.62 g, 4.06 mmol) were combined and dissolved in acetone (50 mL), producing a light yellow solution. Potassium carbonate (0.505 g, 3.65 mmol) was added and the mixture was heated to reflux for 40 hours. The mixture was filtered using vacuum filtration, and the solvent was removed from the filtrate by rotovap. The crude product was purified with silica gel column chromatography with CH2Cl2: hexanes (v/v 5:1) as eluent to afford the product as a yellow oil, which was dried by vacuum. Yield: 0.152 g (12.2%). 1H-NMR (CDCl3) δ (ppm): 8.2 (s, 1H, Ar) 8.1 (d, 1H, Ar), 7.7 (s, 2H, Ar) 7.6 (t, 1H, Ar), 7.5 (d, 1H, Ar), 7.4 (t, 1H, Ar), 5.5 (s, 2H, O—CH2), 4.0 (t, 2H, CH2—O), 2.4 (t, 2H, CH2—C═O), 1.8 (m, 2H, CH2), 1.6 (m, 2H, CH2), 1.6 (s, 18H, CH3), 1.4 (m, 2H, CH2), 1.3 (m, 10H, CH2). 13C-NMR (CDCl3) δ (ppm): 173.5, 165.4, 159.3, 147.9, 134.1, 133.7, 132.7, 129.4, 129.1, 125.4, 122.9, 119.5, 81.9, 68.8, 63.1, 34.5, 29.9, 29.8, 29.7, 29.6, 29.5, 29.4, 28.5, 26.3, 25.3.

Workup

  1. customproducing a light yellow solution
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 40 hours
  4. filtrationThe mixture was filtered
  5. filtrationvacuum filtration
  6. customthe solvent was removed from the filtrate by rotovap
  7. customThe crude product was purified with silica gel column chromatography with CH2Cl2

Sources & evidence

ORD record
ord-9916b81e8e1a42bfb6193c4e3ec2dd71
Source dataset
uspto-grants-2011_12
Patent number
US08076125B2

Reaction notes

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