Methacrylic Acid → 3'-(2-Methylacryloyloxy)biphenyl-3-yl 2-methylacrylate

HRID 1873383Notes

Reaction equation

HRID 1873383 reaction equation
OCCCO[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15](O)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[C:19]([OH:24])(=[O:23])[C:20]([CH3:22])=[CH2:21].C1(N=C=N[CH:34]2[CH2:39][CH2:38]CCC2)CCCCC1.O.O.C(O)(=O)[C:43]([OH:45])=[O:44]>C1(C)C=CC=CC=1>[CH3:21][C:20](=[CH2:22])[C:19]([O:24][C:16]1[CH:17]=[C:12]([C:9]2[CH:8]=[CH:7][CH:6]=[C:11]([O:45][C:43](=[O:44])[C:39]([CH3:38])=[CH2:34])[CH:10]=2)[CH:13]=[CH:14][CH:15]=1)=[O:23]

Participants

6

Reactant 4

HCID 4093Methacrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 61373Oxalic acid dihydrateHCID 160378654'-(3-Hydroxypropoxy)biphenyl-4-ol

Product 1

HCID 582396283'-(2-Methylacryloyloxy)biphenyl-3-yl 2-methylacrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.50 g (18.4 mmol) of 4′-(3-hydroxypropoxy)biphenyl-4-ol, 6.5 ml (0.766 mol) of methacrylic acid and 0.5 g of N,N-dimethylaminopyridine (DMAP) are initially introduced in 250 ml of toluene, a solution of 16.0 g (0.775 mol) of N,N′-dicyclohexylcarbodiimide is added with ice-cooling, and the mixture is stirred overnight at room temp. After addition of 6.5 g of oxalic acid dihydrate, the batch is stirred for 1 h and filtered, and the filtrate is evaporated. The residue is filtered through silica gel with heptane/ethyl acetate (2:1) and recrystallised from diethyl ether, giving 3′-(2-methylacryloyloxy)biphenyl-3-yl 2-methylacrylate as colourless crystals of m.p. 102° C.

Workup

  1. temperaturecooling
  2. stirringthe batch is stirred for 1 h
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. filtrationThe residue is filtered through silica gel with heptane/ethyl acetate (2:1)
  6. customrecrystallised from diethyl ether

Sources & evidence

ORD record
ord-d3c5a1e042ad4b8d88621ad03cedc4d5
Source dataset
uspto-grants-2012_11
Patent number
US08304035B2

Reaction notes

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