Dichloromethane methanol → 1-Naphthalenecarboxylic acid, 4-formyl-, methyl ester

HRID 1950713Notes

Reaction equation

HRID 1950713 reaction equation
[CH:1](/[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:10]=1)=C\C1C=CC=CC=1.C(Cl)Cl.C[OH:27]>>[CH:1]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:10]=1)=[O:27]

Participants

3

Reactant 2

HCID 21226129Dichloromethane methanolHCID 66824254(E)-methyl 4-styryl-1-naphthoate

Product 1

HCID 103308541-Naphthalenecarboxylic acid, 4-formyl-, methyl esterYield 80%

Procedure

A solution of (E)-methyl 4-styryl-1-naphthoate (Preparation 2, 1.31 g, 2.0 mmol) in 3:1 CH2Cl2/MeOH (40 mL) was cooled to −78° C. Sample was subjected to ozonylysis for 10 minutes until blue color was noted. Reaction was quenched with dimethyl sulfide (400 μL) and allowed to warm to room temperature. The residue was purified by chromatography on silica gel eluting from 100% heptane to 50:50 EtOAc:heptane to afford a solid (0.78 g, 80%). 1H NMR (CDCl3) δ ppm: 10.52 (1H), 9.28 (1H), 8.83 (1H), 8.22 (1H), 8.04 (1H), 7.79-7.70 (2H), 4.08 (3H).

Workup

  1. customReaction
  2. customwas quenched with dimethyl sulfide (400 μL)
  3. customThe residue was purified by chromatography on silica gel eluting from 100% heptane to 50:50 EtOAc

Sources & evidence

ORD record
ord-7685f6ae50b14fbaabdc4184ded4840a
Source dataset
uspto-grants-2013_03
Patent number
US08404649B2

Reaction notes

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