Acetic Acid → Methyl 6-Acetoxymethyl-2-naphthoate

HRID 1263297Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]([OH:18])=[O:17])[CH:10]=[CH:9]2)(=[O:3])[CH3:2].[CH3:19]N(N=O)C(N)=O.[OH-].[K+].CC(O)=O>CCOCC>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:10]=[CH:9]2)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 1.08 g (4.43 mmol) of 6-acetoxymethyl-2-naphthoic acid in 150 mL of Et2O at 0° C. was added a cold solution of CH2N2 in Et2O which was prepared from 2.0 g (19 mmol) of N-methyl-N-nitrosourea and 30 mL of 40% aqueous KOH. The mixture was stirred at 0° C. for 10 min when all the solid went into solution. Excess CH2N2 was decomposed with HOAc. The reaction mixture was dried over Na2SO4 and concentrated to give 1.6 g of a white solid, which was purified on 100 g of silica gel (50% EtOAc/hexane) to give 1.04 g (91% yield) of the pure methyl ester. A portion was recrystallized from EtOAc/hexane to give white plates: mp 115°-116° C.; IR (mull) 1720, 1300, 1260, 1200, 1140, 1100, 1040, 980, 940, 900, 840, 820, 760 cm-1 ; 1 H NMR (CDCl3) δ2.15 (s, 3, CH3CO2), 3.98 (s, 3, CO2CH3), 5.28 (s, 2, CH2O), 7.3-8.7 (m, 6, ArH); MS calcd for C15H14O4 258.0892, found 258.0872.

Workup

dry with materialThe reaction mixture was dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-af38a08731014dc9b9497139bb050166
Source dataset: uspto-grants-1984_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04456618

Reaction notes

Loading…