Hydrochloric Acid → HCID 59512340, compound

HRID 1158454Notes

Reaction equation

HRID 1158454 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:9]2[O:10][CH2:11][CH2:12][O:13][C:8]=2[CH:7]=1)=[O:5])C.Cl>O1CCOCC1.[OH-].[Na+]>[CH3:11][O:10][CH2:9][CH2:8][CH2:7][O:16][C:14]1[C:9]2[O:10][CH2:11][CH2:12][O:13][C:8]=2[CH:7]=[C:6]([C:4]([OH:3])=[O:5])[CH:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53689643HCID 53689643, compound

Product 1

HCID 59512340HCID 59512340, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 8-hydroxy-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid ethyl ester (1.85 g, 6.24 mmol) in dioxane (10 mL) and 2N NaOH (5.0 mL) is stirred at 60° C. over 1 h, then cooled to room temperature and acidified (pH 1) with 2N HCl. Volatiles are removed under reduced pressure to afford a suspension. The precipitate is filtered, washed with ice-water and dried in vacuo overnight to give the title product as white solid. TLC, Rf (hexane/AcOEt 2:1+1% AcOH)=0.07. MS: 267.0 [M−H]+. 1H-NMR (DMSO-d6): δ 1.96 (m, 2H), 3.26 (s, 3H), 3.48 (m, 2H), 4.05 (m, 2H), 4.27 (m, 2H), 4.31 (m, 2H), 7.07 (d, 1H9, 7.11 (d, 1H), 12.8 (s, br, 1H) ppm.

Workup

  1. temperaturecooled to room temperature
  2. customVolatiles are removed under reduced pressure
  3. customto afford a suspension
  4. filtrationThe precipitate is filtered
  5. washwashed with ice-water
  6. customdried in vacuo overnight

Sources & evidence

ORD record
ord-50cb0aed79c0454ab3dea2943cb1a3d9
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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