Hydrochloric Acid → HCID 69991613, compound

HRID 1250106Notes

Reaction equation

HRID 1250106 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:31]1[C:32]([CH3:38])=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1.Cl>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH2:6]([O:5][C:1](=[O:4])/[CH:2]=[CH:3]/[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[C:32]=1[CH3:38])[CH3:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 111714303-Bromo-2-methylphenol

Product 1

HCID 69991613HCID 69991613, compoundYield 43.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
82 °C

Procedure

Ethyl acrylate (1.16 mL, 10.7 mmol), palladium acetate (60.1 mg, 0.27 mmol), tri-o-tolylphosphine (160 mg, 0.54 mmol) and triethylamine (1.62 mL) were added to a solution of 3-bromo-2-methyl phenol (1 g, 5.35 mmol) in acetonitrile (2.5 mL) under a nitrogen atmosphere. The mixture was heated at 82° C. for 16 hours and cooled. 1N Hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried under sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave trans-3-(3-hydroxy-2-methylphenyl)acrylic acid ethyl ester as a clear oil (480 mg, 43.5%).

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. customdried under sodium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification by flash chromatography
  7. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-a7f0cb2db7854c74ad3316762ce24953
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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