Hydrochloric Acid → HCID 15124026, compound

HRID 1084874Notes

Reaction equation

HRID 1084874 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:24])=[C:8]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:9]=[C:10]([C:11](=[O:19])[C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:5]=2[O:4][C:3]=1[C:25]([O:27]CC)=[O:26].[OH-].[K+].Cl>O>[CH3:1][C:2]1[C:6]2[C:7]([OH:24])=[C:8]([C:20]([CH3:23])([CH3:21])[CH3:22])[CH:9]=[C:10]([C:11](=[O:19])[C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)[C:5]=2[O:4][C:3]=1[C:25]([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15124025HCID 15124025, compound2×

Product 1

HCID 15124026HCID 15124026, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 3-methyl-4-hydroxy-5-tert-butyl-7-p-chlorobenzoylbenzofuran-2-carboxylate, compound 17 (0.322 g, 0.79 mmol) was suspended in a solution of potassium hydroxide (0.151 g, 2.69 mmol) in water (15 mL) and heated to reflux for 2.5 hours. The resulting solution was cooled in an ice bath and acidified with 2N HCl. The product precipitated and 3-methyl-4-hydroxy-5-tert-butyl-7-p-chlorobenoylbenzofuran-2-carboxylic acid, compound 18 was collected by filtration and allowed to air dry. mp 214°-216° C.; 1H NMR (DMSO-d6) d 1.44 (9H, s), 2.78 (3H, s), 5.78 (1H, s), 7.6 (2H, d, J=8 Hz), 7.62 (1H, s), 7.74 (2H, d, J=8 Hz).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2.5 hours
  3. temperatureThe resulting solution was cooled in an ice bath
  4. customThe product precipitated
  5. filtration3-methyl-4-hydroxy-5-tert-butyl-7-p-chlorobenoylbenzofuran-2-carboxylic acid, compound 18 was collected by filtration
  6. customto air dry

Sources & evidence

ORD record
ord-97cb3d63608244f995bc353f7135e5eb
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

Loading…