Acrylic Acid → 4-Methoxy cinnamic acid

HRID 2356

Reaction equation

HRID 2356 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].C(N(CC)CC)C>Cl[Pd]Cl.O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:12]=[CH:11][C:10]([OH:14])=[O:13])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 6581Acrylic AcidHCID 77304-BromoanisoleHCID 8471Triethylamine

Product 1

HCID 132454-Methoxy cinnamic acidYield 81.2%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

p-bromo anisole (8.4 g), acrylic acid (3.9 g), water (13.5 g), PdCl2 (0.3 mg) and triethyamine (14.3 g, 89.3% pure by titration, the balance being water, recovered by phase separation from a previous run) were charged into an autoclave and heated for 2 hours at 130° C. The work up detailed in Example 1 gave 6.5 g (81%) of >98% pure p-methoxy cinnamic acid.

Workup

  1. customrecovered by phase separation from a previous run)
  2. additionwere charged into an autoclave

Sources & evidence

ORD record
ord-623e76f5d131438c908eae7b5ce8e7ac
Source dataset
uspto-grants-1998_03
Patent number
US05728865

Linked notes

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