Ethanol → HCID 69226285, compound

HRID 916316Notes

Reaction equation

HRID 916316 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[CH2:15](O)[CH3:16].S(=O)(=O)(O)O>C(OCC)(=O)C>[CH2:15]([O:13][C:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([F:1])=[CH:3][CH:4]=1)=[O:14])[CH3:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 684484-Fluoro-1-naphthoic acid

Product 1

HCID 69226285HCID 69226285, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Fluoro-1-naphthoic acid (190 mg, 1.0 mmol) was transferred to a Pyrex tube and ethanol (0.6 mL) was added followed by conc. sulphuric acid (0.1 mL). The tube was capped and the reaction tube was exposed two times to microwave irradiation (2×120° C., 5 min). The reaction mixture was transferred to a separation funnel with ethyl acetate and washed with 2 M NaOH. The aqueous phase was acidified with 2 M HCl and extracted with ethyl acetate. The organic phases were collected, dried over Na2SO4, filtered and concentrated to yield 4-fluoronaphthalene-1-carboxylic acid ethyl ester (154BG85-11, 156 mg, 72%).

Workup

  1. additionwas added
  2. customThe tube was capped
  3. customirradiation (2×120° C., 5 min)
  4. washwashed with 2 M NaOH
  5. extractionextracted with ethyl acetate
  6. customThe organic phases were collected
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7fb80d3e7da84f0db34d46347f86e554
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

Loading…