Resorcinol → 4-((3-Hydroxyphenoxy)carbonyl)phenyl 4-(decyloxy)benzoate

HRID 417786Notes

Reaction equation

HRID 417786 reaction equation
[CH2:1]([O:11][C:12]1[CH:29]=[CH:28][C:15]([C:16]([O:18][C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(Cl)(=O)C(Cl)=O.[C:36]1([CH:43]=[CH:42][CH:41]=[C:39](O)[CH:38]=1)[OH:37].C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:1]([O:11][C:12]1[CH:29]=[CH:28][C:15]([C:16]([O:18][C:19]2[CH:27]=[CH:26][C:22]([C:23]([O:25][C:39]3[CH:41]=[CH:42][CH:43]=[C:36]([OH:37])[CH:38]=3)=[O:24])=[CH:21][CH:20]=2)=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 5054ResorcinolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 158098324-(4-(Decyloxy)benzoyloxy)benzoic acid

Product 1

HCID 666481824-((3-Hydroxyphenoxy)carbonyl)phenyl 4-(decyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

Compound 16 (2.05 g, 5.2 mmol) was suspended in toluene (100 mL), and refluxed with oxalyl chloride (2.0 mL, 23.2 mmol) for five hours. Volatile components were removed, and the white solid was taken in CH2Cl2 (50 mL) and added dropwise while stirring to a solution containing resorcinol (1.23 g, 11.2 mmol), triethylamine (5.4 mL, 39 mmol), and DMAP (0.06 g, 0.52 mmol). Following stirring at room temperature for 12 hours, the mixture was then refluxed for twenty four hours. The solvent was removed under reduced pressure, and the residue purified by column chromatography (CH2Cl2:EtOH, 10:0.03, and then CH2Cl2:EtOH, 10:0.3). The product was then recrystallized from ethanol. Yield (1.6 g, 64%). 1H NMR: δH (CDCl3; 300 MHz): 0.92 (3 H, t, 3J=6.9 Hz, CH3), 1.23-1.60 (14 H, m, CH2), 1.86 (2 H, m, O—CH2—CH2), 4.07 (2 H, t, 3J=6.5 Hz, O—CH2), 6.15 (1 H, bs, OH), 6.69 (2 H, m, Ar—H), 6.78 (1 H, d, 3J=8.3 Hz, Ar—H), 7.01 (2 H, d, 3J=8.9 Hz, Ar—H), 7.25 (1 H, t, 3J=8.5 Hz, Ar—H), 7.38 (2 H, d, 3J=8.8 Hz, Ar—H), 8.18 (2 H, d,3J=8.9 Hz, Ar—H), 8.27 (2 H, d, 3J=8.8 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 14.5, 23.1, 26.4, 29.5, 29.7, 29.8, 30.0, 32.3, 68.8, 109.8, 113.8, 113.9, 114.9, 121.2, 122.6, 127.2, 130.5, 132.3, 132.9, 152.0, 155.8, 157.4, 164.3, 165.0, 165.3.

Workup

  1. customVolatile components were removed
  2. additionadded dropwise
  3. stirringFollowing stirring at room temperature for 12 hours
  4. temperaturethe mixture was then refluxed for twenty four hours
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified by column chromatography (CH2Cl2
  7. customThe product was then recrystallized from ethanol
  8. customYield (1.6 g, 64%)

Sources & evidence

ORD record
ord-6568411c596e4639902a06358c8b2ae3
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Reaction notes

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