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Methyl Acrylate → 4-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid

HRID 1669734
Notes
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Reaction equation

HRID 1669734 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:41]([O:45][CH3:46])(=[O:44])[CH:42]=[CH2:43]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:46][O:45][C:41](=[O:44])/[CH:42]=[CH:43]/[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 2825914-Bromo-1-naphthoic acid

Product 1

HCID 673480204-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acidYield 85.3%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-1-naphthalenecarboxylic acid (9.42 g), triethylamine (25 ml), palladium acetate (0.85 g), triphenylphosphine (0.98 g) and methyl acrylate (9.68 g) in anhydrous DMF (95 ml) was heated to 100° C. for 1 h under nitrogen. The mixture was allowed to cool to room temperature, filtered through Celite and washed with diethyl ether/water. The filtrate was extracted with ether, then with EtOAc. The aqueous phase was acidified to approximately pH 1 with 2 M aqueous hydrogen chloride. The solid was filtered, washed with water and dried at 40° C. under vacuum, to afford the title compound (8.2 g).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through Celite
  3. washwashed with diethyl ether/water
  4. extractionThe filtrate was extracted with ether
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-5b46b6b625264768b62c83969ac50b72
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07989629B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes