Hydrochloric Acid → HCID 22313303, compound

HRID 965830Notes

Reaction equation

HRID 965830 reaction equation
[OH-:1].[K+].[CH2:3]([CH:5]1[CH2:10][O:9][C:8]2[CH:11]=[CH:12][C:13]([C:15]#N)=[CH:14][C:7]=2[O:6]1)[CH3:4].C(O)C.Cl.[OH2:21]>>[CH2:3]([CH:5]1[CH2:10][O:9][C:8]2[CH:11]=[CH:12][C:13]([C:15]([OH:21])=[O:1])=[CH:14][C:7]=2[O:6]1)[CH3:4]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962Water2×HCID 14797Potassium HydroxideHCID 22313315HCID 22313315, compound

Product 1

HCID 22313303HCID 22313303, compoundYield 92%

Conditions

Temperature
80 °C

Procedure

KOH (218 mg, 3.9 mmol) is added to a mixture of 3-ethyl-2,3-dihydro-1,4-benzodioxine-6-carbonitrile (247 mg, 1.3 mmol), ethanol (3 mL) and water (1 mL). The resulting mixture is heated to 80° C. for 24 hours. The reaction is allowed to cool, diluted with water (2 mL) and acidified to pH<2 with concentrated HCl. The resulting solid is filtered, washed with water and dried at 60° C. under vacuum to give 3-ethyl-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid as a white solid (249 mg, 92%). 1H NMR (400 MHz, DMSO-d6) δ 12.66, 7.43, 7.37, 6.95, 4.38, 4.10, 3.95, 1.64, 1.01.

Workup

  1. temperatureto cool
  2. filtrationThe resulting solid is filtered
  3. washwashed with water
  4. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-35db9b855e32402d952d63ec99a8ab8a
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

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