Hydrochloric Acid → 4-{[4-({6-[2-(Acryloyloxy)-1-methylethoxy]-6-oxohexyl}oxy)benzoyl]oxy}-2-methylphenyl 4-({6-[2-(acryloyloxy)-1-methylethoxy]-6-oxohexyl}oxy)benzoate

HRID 424305Notes

Reaction equation

HRID 424305 reaction equation
[C:1]([O:5][CH2:6][CH:7]([O:9][C:10](=[O:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br)[CH3:8])(=[O:4])[CH:2]=[CH2:3].[OH:18][C:19]1[CH:44]=[CH:43][C:22]([C:23]([O:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33](=[O:41])[C:34]3[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=3)=[CH:28][C:27]=2[CH3:42])=[O:24])=[CH:21][CH:20]=1.[C:45]([O-:48])([O-:47])=O.[K+].[K+].Cl>CC(=O)CC>[C:1]([O:5][CH2:6][CH:7]([CH3:8])[O:9][C:10](=[O:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33](=[O:41])[C:34]3[CH:39]=[CH:38][C:37]([O:40][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:45]([O:48][CH:7]([CH3:8])[CH2:6][O:5][C:1](=[O:4])[CH:2]=[CH2:3])=[O:47])=[CH:36][CH:35]=3)=[CH:28][C:27]=2[CH3:42])=[O:24])=[CH:43][CH:44]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 109921202-Methyl-1,4-phenylene bis(4-hydroxybenzoate)HCID 590050292-[(6-Bromohexanoyl)oxy]propyl acrylate

Product 1

HCID 590050254-{[4-({6-[2-(Acryloyloxy)-1-methylethoxy]-6-oxohexyl}oxy)benzoyl]oxy}-2-methylphenyl 4-({6-[2-(acryloyloxy)-1-methylethoxy]-6-oxohexyl}oxy)benzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-[(6-bromohexanoyl)oxy]propyl acrylate (4.15 g), 4-[(4-hydroxybenzoyl)oxy]-2-methylphenyl 4-hydroxybenzoate (2.24 g) and K2CO3 (2.55 g) in 2-butanone (40 ml) was heated at 100° C. overnight. The reaction mixture was poured into HCl 1N (50 ml) and extracted twice with 80 ml of diethylether. The etheral extracts were dried over Na2SO4 and evaporated to dryness. The obtained pasty residue was purified by silica column chromatography to give nearly pure 4-{[4-({6-[2-(acryloyloxy)-1-methylethoxy]-6-oxohexyl}oxy)benzoyl]oxy}-2-methylphenyl 4-({6-[2-(acryloyloxy)-1-methylethoxy]-6-oxohexyl}oxy)benzoate as slightly yellow oil.

Workup

  1. extractionextracted twice with 80 ml of diethylether
  2. dry with materialThe etheral extracts were dried over Na2SO4
  3. customevaporated to dryness
  4. customThe obtained pasty residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-c964ac44e6d444afb239752f5154e044
Source dataset
uspto-grants-2012_01
Patent number
US08105662B2

Reaction notes

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