Methyl Gallate → HCID 58473600, compound

HRID 1810819Notes

Reaction equation

HRID 1810819 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].CC1C=CC(S(O[CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH3:58])(=O)=O)=CC=1.[CH2:59]1[O:76][CH2:75][CH2:74][O:73][CH2:72][CH2:71][O:70][CH2:69][CH2:68][O:67][CH2:66][CH2:65][O:64][CH2:63][CH2:62][O:61][CH2:60]1>CC(C)=O>[CH3:58][O:57][CH2:56][CH2:55][O:54][CH2:53][CH2:52][O:51][CH2:50][CH2:49][O:48][CH2:47][CH2:46][O:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37][O:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH3:58])[C:11]=1[O:12][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:59][O:76][CH2:75][CH2:74][O:73][CH2:72][CH2:71][O:70][CH2:69][CH2:68][O:67][CH2:66][CH2:65][O:64][CH2:63][CH2:62][O:61][CH2:60][CH2:38][O:39][CH3:40])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7428Methyl GallateHCID 2855718-Crown-6HCID 58473715HCID 58473715, compound

Product 1

HCID 58473600HCID 58473600, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 3,4,5-trihydroxybenzoate (200 mg, 1.1 mmol), 2,5,8,11,14,17,20,23,26,29,32-undecaoxatetratriacontan-34-yl 4-methylbenzenesulfonate (2.58 g, 3.85 mmol), and 18-crown-6 (100 mg, 0.38 mmol) are transferred to a round bottom flask equipped with a Teflon-coated stirbar. Acetone (10 mL) is added and the flask is equipped with a reflux condenser. The mixture is refluxed with constant stirring overnight. The next day silica (4 g) is added and the solvent evaporated. After purification by column chromatography, a clear oil is obtained (887 mg, 48% yield).

Workup

  1. customthe flask is equipped with a reflux condenser
  2. temperatureThe mixture is refluxed
  3. additionThe next day silica (4 g) is added
  4. customthe solvent evaporated
  5. customAfter purification by column chromatography
  6. customa clear oil is obtained (887 mg, 48% yield)

Sources & evidence

ORD record
ord-11e38784566c4ef09fb40ec60ff73508
Source dataset
uspto-grants-2013_01
Patent number
US08362193B2

Reaction notes

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