1-Hydroxy-2-naphthoic acid → 4-Methoxybenzyl 1-hydroxynaphthalene-2-carboxylate

HRID 366797Notes

Reaction equation

HRID 366797 reaction equation
[Na].[OH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13]([OH:15])=[O:14].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1>CS(C)=O>[OH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13]([O:15][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)=[O:14]

Participants

5

Reactant 3

HCID 68441-Hydroxy-2-naphthoic acidHCID 699934-Methyloxybenzyl chlorideHCID 5360545Sodium

Product 1

HCID 107811084-Methoxybenzyl 1-hydroxynaphthalene-2-carboxylateYield 66,431.703%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

(This is a compound 15a of Scheme 1). A suspension of powdered sodium salt of 1-hydroxynaphthalene-2-carboxylic acid (1) (61.3 g, 0.29 mmol) in DMSO (205 mL) was treated with 4-methoxybenzyl chloride (98%, 46.7 g, 0.29 mmol) and then stirred at 70° C. for 1 h. After cooling, the mixture was poured into dilute aqueous KHCO3 (3.5 L) and the resulting precipitate was collected, washed with water and dried. The solid was extracted with boiling petroleum ether (bp 60-65° C., 1100 mL), treated with decolourising charcoal and the filtered solution was cooled for a prolonged period at 0° C. to provide crude 4-methoxybenzyl 1-hydroxynaphthalene-2-carboxylate (2) (59.4 g, 66%), suitable for further use. A sample was recrystallised from iPr2O/petroleum ether, mp 92-93° C. 1H NMR [(CD3)2SO] δ 11.91 (s, 1H, OH), 8.31 (d, J=8.2 Hz, 1H, H-3), 7.92 (d, J=8.1 Hz, 1H, H-4), 7.73 (d, J=8.8 Hz, 1H, ArH), 7.71 (brt, J=7.5 Hz, 1H, ArH), 7.61 (br t, J=1.6 Hz, 1H, ArH), 6.99 (d, J=8.6 Hz, 2H, H-3',5'), 5.40 (s, 2H, CH2), 3.34 (s, 3H, CH3). Anal. Calculated for C19H16O4): C, 74.0; H, 5.2. Found: C, 73.7; H, 5.2%.

Workup

  1. temperatureAfter cooling
  2. customthe resulting precipitate was collected
  3. washwashed with water
  4. customdried
  5. extractionThe solid was extracted with boiling petroleum ether (bp 60-65° C., 1100 mL)
  6. additiontreated with decolourising charcoal
  7. temperaturethe filtered solution was cooled for a prolonged period at 0° C.

Sources & evidence

ORD record
ord-2bf87325784546b9a50207f96d98ceff
Source dataset
uspto-grants-2000_10
Patent number
US06130237

Reaction notes

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