Sodium ethoxide → Ethyl 7-(2-chloroethoxy)-6-methoxy-3-nitro-2-naphthoate

HRID 989354Notes

Reaction equation

HRID 989354 reaction equation
[N+:1]([CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-:3])=[O:2].[O-]CC.[Na+].[Cl:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]([CH:29]=O)[C:22](=[CH:25][C:26]=1[O:27][CH3:28])[CH:23]=O>C(O)C>[Cl:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:22]([CH:23]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:29]2)=[CH:25][C:26]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 116944184-(2-Chloroethoxy)-5-methoxyphthalaldehydeHCID 11804910Ethyl 3-nitropropionate

Product 1

HCID 9968466Ethyl 7-(2-chloroethoxy)-6-methoxy-3-nitro-2-naphthoateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of 2.43 g of ethyl 3-nitropropionate in 15 ml of absolute ethanol cooled using an ice bath, is added 20 mL of 1N sodium ethoxide in ethanol dropwise over 10 minutes keeping the temperature at 0-5° C. A slurry of 4-(2-chloroethoxy)-5-methoxyphthalaldehyde in 5 mL of ethanol is added. The ice bath is removed and the reaction allowed to warm to room temperature and stirred for 16 hours. The reaction is transferred to a beaker with 300 mL of water and neutralized with acetic acid to pH 4. The solid is collected and washed first with water, then with 40 mL of cold ethanol. The solid is dried to provide 2.48 g (70%) of ethyl 7-(2-chloroethoxy)-6-methoxy-3-nitro-2-naphthoate and ethyl 6-(2-chloroethoxy)-7-methoxy-3-nitro-2-naphthoate (1:1 mixture) as a yellow solid, m.p. 119-29° C. dec.

Workup

  1. customat 0-5° C
  2. customThe ice bath is removed
  3. customThe solid is collected
  4. washwashed first with water
  5. customThe solid is dried

Sources & evidence

ORD record
ord-a26690e421fc4e409a0aaf37b84eed63
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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