Hydrochloric Acid → 7-(Benzyloxy)-2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acid

HRID 454462Notes

Reaction equation

HRID 454462 reaction equation
O.O.P([O-])(O)(O)=O.[Na+].[CH2:9]([O:16][C:17]1[C:18]([CH:27]=[O:28])=[CH:19][C:20]2[O:25][CH2:24][CH2:23][O:22][C:21]=2[CH:26]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.OO.Cl([O-])=[O:32].[Na+].Cl>C(OCC)(=O)C.O.C(#N)C>[CH2:9]([O:16][C:17]1[C:18]([C:27]([OH:32])=[O:28])=[CH:19][C:20]2[O:25][CH2:24][CH2:23][O:22][C:21]=2[CH:26]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 866592387-(Benzyloxy)-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde

Product 1

HCID 669903867-(Benzyloxy)-2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acidYield 100.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A water (0.60 mL) solution of sodium dihydrogen phosphate dihydrate (0.50 g) was added to an acetonitrile (1.6 mL) suspension of the obtained 7-(benzyloxy)-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde (0.32 g), and a 30% hydrogen peroxide solution (0.20 mL) and a water (0.30 mL) solution of sodium chlorite (0.17 g) were sequentially added thereto under ice-cooling, followed by stirring at the same temperature for 15 minutes and then at room temperature for 1 hour and 30 minutes. The reaction mixture was adjusted to a pH of 1.4 with 1 mol/L hydrochloric acid, and water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.34 g of 7-(benzyloxy)-2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acid as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. waitat room temperature for 1 hour
  3. custom30 minutes
  4. additionwere added
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0998cf5c30f34c718c91fb55acd6a35c
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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