Sodium Hydroxide → 2-(5-methyl-1-benzofuran-3-yl)acetic acid

HRID 402908Notes

Reaction equation

HRID 402908 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:13])[CH:11]=2)[O:6][C:5](=[O:14])[CH:4]=1.[OH-:15].[Na+]>Cl>[CH3:13][C:10]1[CH:9]=[CH:8][C:7]2[O:6][CH:2]=[C:3]([CH2:4][C:5]([OH:14])=[O:15])[C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9074424-(chloromethyl)-6-methyl-2H-chromen-2-one

Product 1

HCID 47369772-(5-methyl-1-benzofuran-3-yl)acetic acidYield 94%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

4-chloromethyl-6-methyl-chromen-2-one (10.4 g, 50.0 mmol) is suspended in a 1.0 M aqueous NaOH solution (400 mL). The reaction mixture is heated under reflux for 30 min. until a clear solution is obtained. The reaction mixture is cooled in an ice bath and carefully neutralized with a 2 M aqueous HCl solution (200 mL). More of a 2 M aqueous HCl solution is added until a white precipitate formed (pH<5). The precipitate is collected by suction filtration, washed with a small amount of an 1 M aqueous HCl solution and dried in vacuo at 50° C. to afford the title compound as a white powder (9.94 g, 47 mmol, 94%). 1H NMR (400 MHz, CDCl3, 298 K): δ=7.63 (s, 1H), 7.39 (d, J=8.3 Hz, 1H), 7.36 (s, 1H), 7.14 (d, J=8.3 Hz, 1H), 3.76 (s, 2H), 2.48 (s, 3H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 30 min. until a clear solution
  3. customis obtained
  4. temperatureThe reaction mixture is cooled in an ice bath
  5. customformed (pH<5)
  6. filtrationThe precipitate is collected by suction filtration
  7. washwashed with a small amount of an 1 M aqueous HCl solution
  8. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-3b16814ccbea4b958b222cde6f036f72
Source dataset
uspto-grants-2014_06
Patent number
US08742132B2

Reaction notes

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