1-Naphthoic acid → HCID 59850847, compound

HRID 2373122Notes

Reaction equation

HRID 2373122 reaction equation
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O[CH2:15][CH2:16][O:17][C:18](=[O:22])[C:19]([CH3:21])=[CH2:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:18]([O:17][CH2:16][CH2:15][O:12][C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:13])(=[O:22])[C:19]([CH3:21])=[CH2:20]

Participants

6

Reactant 4

HCID 68471-Naphthoic acidHCID 10868DicyclohexylcarbodiimideHCID 133602-Hydroxyethyl MethacrylateHCID 86598837HCID 86598837, compound

Product 1

HCID 59850847HCID 59850847, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-napthoic acid (8.0 g, 46 mmol), 2-hydroxyethylmethacrylate (18.1 g, 139 mmol), dimethylamino-pyridine p-toluenesulfonic acid salt (5.5 g, 19 mmol), and anhydrous dichloromethane (45 mL) was cooled to 0° C. under nitrogen, and 1,3-dicyclohexyl-carbodiimide (12.5 g, 60 mmol) were added. After 15 min, the reaction mixture was warmed to ambient and stirred for 3 h. The precipitated urea by-product was filtered, and the filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine. The organic layer was dried (Na2SO4) and concentrated to deposit a gold oil. The product was purified by column chromatography to provide 8.2 g (62% of theory) of a pale yellow oil. 1H NMR (CDCl3): δ 1.90 (s, 3H), 1.55 (m, 2H), 1.70 (m, 2H), 5.60 (s, 1H), 6.20 (s, 1H), 7.55 (m, 3H), 7.90 (d, 1H), 8.05 (d, 1H), 8.20 (d, 1H), 8.90 (d, 1H).

Workup

  1. temperaturethe reaction mixture was warmed to ambient and
  2. filtrationThe precipitated urea by-product was filtered
  3. washthe filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography
  7. customto provide 8.2 g (62% of theory) of a pale yellow oil

Sources & evidence

ORD record
ord-46be3e3a4e6f4c9ea1ec1a5bcc4541f0
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

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