Hydrochloric Acid → 6-[(1-Oxo-2-propen-1-yl)oxy]-2-naphthalenecarboxylic acid

HRID 2245901Notes

Reaction equation

HRID 2245901 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[OH-].[Na+].[C:17](Cl)(=[O:20])[CH:18]=[CH2:19].Cl>O>[C:17]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2)(=[O:20])[CH:18]=[CH2:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 592169606-[(1-Oxo-2-propen-1-yl)oxy]-2-naphthalenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 3.00 g (16 mmol) of 6-hydroxy-2-naphthoic acid, 40 mmol of sodium hydroxide, and 16 g of water, 1.59 g (18 mmol) of acryloyl chloride was added at 20° C., and the reaction was performed for 3 hours. After the reaction, the mixture was acidified by adding 4-mol/l hydrochloric acid dropwise and chilled with ice-water. The resultant precipitate was collected by filtration, dried in an oven at 40° C., and recrystallized from methanol-THF (2:3) mixed solvent to yield the desired product, 6-acryloyloxy-2-naphthoic acid, as while solid (2.07 g, Yield: 53.6%).

Workup

  1. additionwas added at 20° C.
  2. customAfter the reaction
  3. filtrationThe resultant precipitate was collected by filtration
  4. customdried in an oven at 40° C.
  5. customrecrystallized from methanol-THF (2:3)
  6. additionmixed solvent

Sources & evidence

ORD record
ord-e1aa229c4456453096f7adaa35bc8f80
Source dataset
uspto-grants-2010_03
Patent number
US07683203B2

Reaction notes

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