Hydroquinone → 4-{[6-(Methacryloyloxy)hexyl]oxy}benzenecarboxylic acid
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1.[C:18](O)(=[O:22])[C:19]([CH3:21])=[CH2:20].C1(C=CC(O)=CC=1)O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl.O>[CH3:21][C:19](=[CH2:20])[C:18]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:16][CH:17]=1)=[O:22]Participants
7
Procedure
71.5 g (0.3 mol) of 4-(6-hydroxy-hexyloxy)-benzoic acid and 101.5 g (1.18 mol) of methacrylic acid were dissolved in 950 ml of chloroform. After the addition of 7.2 g (0.07 mol) of hydroquinone and 7.2 g (0.04 mol) of p-toluenesulphonic acid the batch was boiled under reflux on a water separator for 48 hours. The clear brown solution was subsequently evaporated, the residue was taken up in 1.5 l of diethyl ether, filtered and shaken five time with 300 ml of H2O each time. The organic phase was dried over Na2SO4, evaporated and the residue was recrystallized twice from methanol. After drying at 40° C. in a water-jet vacuum 47.33 g of 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoic acid remained behind as a white powder; m.p. 83° C.
Workup
- customThe clear brown solution was subsequently evaporated
- filtrationfiltered
- dry with materialThe organic phase was dried over Na2SO4
- customevaporated
- customthe residue was recrystallized twice from methanol
- dry with materialAfter drying at 40° C. in a water-jet vacuum 47.33 g of 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoic acid
Sources & evidence
- ORD record
- ord-3f2b8f77045b48e3ad010e2e72b2d037
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06335409B1
Reaction notes
Loading…