Triethylamine → 5-[4-(6-Acryloyloxyhexyloxy)benzoyloxy]-2-hydroxybenzoic acid 6-acryloyloxyhexyl ester

HRID 352269Notes

Reaction equation

HRID 352269 reaction equation
S(Cl)(C)(=O)=O.[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(=[O:9])[CH:7]=[CH2:8].C(N(CC)CC)C.[C:34]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:45][C:46](=[O:55])[C:47]1[CH:52]=[C:51](O)[CH:50]=[CH:49][C:48]=1[OH:54])(=[O:37])[CH:35]=[CH2:36]>C1COCC1>[C:34]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:45][C:46](=[O:55])[C:47]1[CH:52]=[C:51]([O:23][C:22](=[O:24])[C:21]2[CH:20]=[CH:19][C:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:6](=[O:9])[CH:7]=[CH2:8])=[CH:26][CH:25]=2)[CH:50]=[CH:49][C:48]=1[OH:54])(=[O:37])[CH:35]=[CH2:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidHCID 227090752,5-Dihydroxybenzoic-6-acryloyloxyhexyl ester

Product 1

HCID 207309215-[4-(6-Acryloyloxyhexyloxy)benzoyloxy]-2-hydroxybenzoic acid 6-acryloyloxyhexyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-25 °C

Procedure

A solution of mesyl chloride (3.44 g) in 50 ml of dry THF was added dropwise under argon to a cooled (−25° C.) solution of 4-(6-acryloyloxyhexyloxy)benzoic acid (8.35 g) and triethylamine (6.07 g) in 100 ml of dry THF. After complete addition (15 min), the reaction mixture was stirred for a further 30 min at −25° C., treated with a solution of 2,5-dihydroxybenzoic-6-acryloyloxyhexyl ester in 50 ml of dry THF and further stirred at −25° C. for 4 h. The reaction mixture was then filtered through celite and the solvent was removed by evaporation. The filtrate was purified by flash chromatography using a short silica-gel column and dichloromethane/diethylether (39/1) as eluent to give 10.8 g of 5-[4-(6-acryloyloxyhexyloxy)benzoyloxy]-2-hydroxybenzoic acid 6-acryloyloxyhexyl ester as a slightly beige oil.

Workup

  1. additionAfter complete addition (15 min)
  2. stirringfurther stirred at −25° C. for 4 h
  3. filtrationThe reaction mixture was then filtered through celite
  4. customthe solvent was removed by evaporation
  5. customThe filtrate was purified by flash chromatography

Sources & evidence

ORD record
ord-551d57505b434dd1ad09a0e8ce9c6206
Source dataset
uspto-grants-2004_06
Patent number
US06746729B1

Reaction notes

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