Water → 1-[4'-(4"-Acryloxybutoxy)benzoyloxy]-4-[4'-(2"-acryloxyethoxy)-benzoyloxy]benzene

HRID 355600Notes

Reaction equation

HRID 355600 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([O:11][CH2:12][CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)(=[O:10])[CH:8]=[CH2:9].[C:24]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:49]=[CH:48][C:37]([C:38]([O:40][C:41]2[CH:46]=[CH:45][C:44](O)=[CH:43][CH:42]=2)=[O:39])=[CH:36][CH:35]=1)(=[O:27])[CH:25]=[CH2:26].O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:24]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:35]=[CH:36][C:37]([C:38]([O:40][C:41]2[CH:46]=[CH:45][C:44]([O:20][C:19](=[O:21])[C:18]3[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][O:11][C:7](=[O:10])[CH:8]=[CH2:9])=[CH:23][CH:22]=3)=[CH:43][CH:42]=2)=[O:39])=[CH:48][CH:49]=1)(=[O:27])[CH:25]=[CH2:26]

Participants

7

Reactant 4

HCID 962WaterHCID 65578Oxalyl chlorideHCID 152185974-[4'-(4-Acryloxybutoxy)benzoyloxy]phenolHCID 155446054-(2-Prop-2-enoyloxyethoxy)benzoic acid

Product 1

HCID 152185981-[4'-(4"-Acryloxybutoxy)benzoyloxy]-4-[4'-(2"-acryloxyethoxy)-benzoyloxy]benzeneYield 83.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×

Procedure

Oxalyl chloride (10 ml) is added at 0° C. to 4-(2'-acryloxyethoxy)-benzoic acid (4.3 g; 16.3 mmol), and the mixture is stirred until the evolution of gas subsides (30 min). The excess oxalyl chloride is removed by distillation in a water-pump vacuum, the acid chloride is taken up in toluene (10 ml), the toluene solution is added at 0° C. to a solution of (3) (5.8 g; 16.3 mmol) in pyridine (10 ml) and toluene (5 ml), and the mixture is subsequently stirred at room temperature for 13 hours. The reaction mixture is then transferred into water (200 ml), and the mixture is extracted twice with dichloromethane (50 ml each time). The organic extracts are dried using calcium chloride, hydroquinone (50 mg) is added to the filtrate, and the mixture is evaporated in a water-pump vacuum. The residue is chromatographed on silica gel (toluene/ethyl acetate (5:1), giving 7.8 g (83%) of (4).

Workup

  1. customThe excess oxalyl chloride is removed by distillation in a water-pump vacuum
  2. stirringthe mixture is subsequently stirred at room temperature for 13 hours
  3. extractionthe mixture is extracted twice with dichloromethane (50 ml each time)
  4. customThe organic extracts are dried
  5. additionis added to the filtrate
  6. customthe mixture is evaporated in a water-pump vacuum
  7. customThe residue is chromatographed on silica gel (toluene/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-ede8c3aa81184a1dbe1c2f1dae99382b
Source dataset
uspto-grants-1998_11
Patent number
US05833880

Reaction notes

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