Hydrochloric Acid → 1-(2-Phenoxy-ethoxy)-naphthalene-2-carboxylic acid methyl ester

HRID 1889262Notes

Reaction equation

HRID 1889262 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:18]([O:20][CH3:21])=[O:19].Br[CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>CN(C=O)C>[CH3:21][O:20][C:18]([C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[O:7][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 703582-Naphthalenecarboxylic acid, 1-hydroxy-, methyl ester

Product 1

HCID 688461391-(2-Phenoxy-ethoxy)-naphthalene-2-carboxylic acid methyl esterYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 22.81 g cesium carbonate and 7.08 g methyl 1-hydroxy-2-naphthoate in 70 ml abs. DMF was added 7.39 g (2-bromo-ethoxy)-benzene and the mixture was reacted for 16 h at 80° C. The reaction was poured unto ice, neutralized with 2 M hydrochloric acid, and extracted with ethyl acetate twice. The combined organic phases were washed with brine, dried over magnesium sulphate and concentrated in vacuo. The resulting residue was purified by crystallization from pentane to yield 9.60 g of 1-(2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid methyl ester.

Workup

  1. customthe mixture was reacted for 16 h at 80° C
  2. additionThe reaction was poured unto ice
  3. extractionextracted with ethyl acetate twice
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by crystallization from pentane

Sources & evidence

ORD record
ord-7f91b29fbdd74de287e2698eb4929a92
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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