Hydrochloric Acid → 6-[[[4-[(1-Oxo-2-propen-1-yl)oxy]butoxy]carbonyl]oxy]-2-naphthalenecarboxylic acid

HRID 2241788Notes

Reaction equation

HRID 2241788 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+].Cl[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26](=[O:29])[CH:27]=[CH2:28])=[O:19].Cl.C([O-])(=O)C=C.Cl>CN(C=O)C.O>[C:26]([O:25][CH2:24][CH2:23][CH2:22][CH2:21][O:20][C:18]([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:19])(=[O:29])[CH:27]=[CH2:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 855576-Hydroxy-2-naphthoic acidHCID 153761584-[(Chlorocarbonyl)oxy]butyl 2-propenoateHCID 22164742HCID 22164742, compound

Product 1

HCID 592038096-[[[4-[(1-Oxo-2-propen-1-yl)oxy]butoxy]carbonyl]oxy]-2-naphthalenecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The pH of a solution of 100 g (0.53 mol) of 6-hydroxy-2-naphthoic acid in a solvent mixture of 600 ml of water and 500 ml of DMF was adjusted to 10 with 10 percent sodium hydroxide solution at 0° C. 132 g (0.61 mol) of 4-acryloyloxybutyl chloroformate (prepared according to WO 97/00600 A2) was subsequently added dropwise over a period of 2 h, in the course of which the temperature was kept between 0 and 5° C. and the pH at 10 (±0.2 pH unit) by means of 10 percent sodium hydroxide solution. The resulting solution was subsequently diluted with 3 l of water/ice mixture and the pH was adjusted to 5 with concentrated hydrochloric acid. The resulting suspension was filtered, the resulting filtercake was washed with 3 l of water and, after drying, 165.8 g (87% of theory based on the pure acrylate derivative) of a beige-colored powder were obtained, which comprises the compound NAPA shown above and the corresponding acrylate/HCl adduct.

Workup

  1. customwas kept between 0 and 5° C.
  2. filtrationThe resulting suspension was filtered
  3. washthe resulting filtercake was washed with 3 l of water
  4. customafter drying
  5. customwere obtained

Sources & evidence

ORD record
ord-222881038fa349c48a097882e44f1f23
Source dataset
uspto-grants-2010_03
Patent number
US07670505B2

Reaction notes

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