Acrylic Acid → HCID 53700986, compound

HRID 1883175Notes

Reaction equation

HRID 1883175 reaction equation
Br[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[C:20]([OH:24])(=[O:23])[CH:21]=[CH2:22]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH2:7]([O:6][C:4]([C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[CH:22]=[CH:21][C:20]([OH:24])=[O:23])=[O:5])[CH3:8]

Participants

7

Reactant 3

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 80186Ethyl 2-bromobenzoate

Product 1

HCID 53700986HCID 53700986, compoundYield 103%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ethyl o-bromobenzoate (20.0 g), P(o-tol)3 (2.66 g), triethylamine (17.6 g) and acrylic acid (12.6 g) in toluene (70 mL) was added palladium acetate (980 mg) under nitrogen atmosphere, and the mixture was heated at 110° C. for one hour. The reaction solution was filtered, and extracted with a saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was acidified with hydrochloric acid, extracted with ethyl acetate, dried, filtered, and concentrated to give 3-(2-ethoxycarbonylphenyl)acrylic acid (19.8 g, 103%).

Workup

  1. filtrationThe reaction solution was filtered
  2. extractionextracted with a saturated aqueous sodium hydrogen carbonate solution
  3. extractionextracted with ethyl acetate
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aa085dec15974f6e94b738f952abea66
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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