Ethyl Acetate → 1-Naphthalenecarboxylic acid, 4-formyl-, methyl ester

HRID 1950720Notes

Reaction equation

HRID 1950720 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15]Br)=[CH:7][CH:6]=1)=[O:4].C(=O)(O)[O-:18].[Na+].CCOC(C)=O>CS(C)=O.CCCCCC>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]=[O:18])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 103338131-Naphthalenecarboxylic acid, 4-(bromomethyl)-, methyl ester

Product 1

HCID 103308541-Naphthalenecarboxylic acid, 4-formyl-, methyl esterYield 52.17%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 4-bromomethyl-naphthalene-1-carboxylic acid methyl ester (Preparation 51, 10.5 g, 37.63 mmol) in DMSO (99.36 mL) was added sodium bicarbonate (6.32 g, 75.27 mmol) at room temperature. Resulting reaction mixture was heated at 95° C. for 3 hours. Progress of the reaction was monitored by TLC using 10% EtOAc in hexane. Rf of new spot and starting material was 0.7 and 0.8 respectively. After consumption of starting material, reaction mixture was quenched with water (400 mL) and extracted with EtOAc (2×300 mL). Combined organic layer was dried over sodium sulphate and evaporated off in vacuo to get brown colored thick mass. Crude compound was purified by column chromatography using 100-200 mesh silica gel. Desired product was eluted in 4.5% EtOAc in hexane to afford faint green solid (4.2 g, 52.17%). Compound the same as that from Preparation 3.

Workup

  1. customResulting
  2. customreaction mixture
  3. customAfter consumption of starting material, reaction mixture
  4. customwas quenched with water (400 mL)
  5. extractionextracted with EtOAc (2×300 mL)
  6. dry with materialCombined organic layer was dried over sodium sulphate
  7. customevaporated off in vacuo
  8. customto get brown colored thick mass
  9. customCrude compound was purified by column chromatography
  10. washDesired product was eluted in 4.5% EtOAc in hexane

Sources & evidence

ORD record
ord-8680f65090ba4592b3264ea3835a5163
Source dataset
uspto-grants-2013_03
Patent number
US08404649B2

Reaction notes

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