Hydrochloric Acid → 5-(hydroxymethyl)-1,3-benzoxazol-2(3H)-one

HRID 450784

Reaction equation

HRID 450784 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=O.C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1.[BH4-].[Na+].Cl>C1COCC1.O>[OH:7][CH2:5][C:4]1[CH:8]=[CH:9][C:10]2[O:11][C:17](=[O:18])[NH:1][C:2]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 650833-Amino-4-hydroxybenzoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydride

Product 1

HCID 594788815-(hydroxymethyl)-1,3-benzoxazol-2(3H)-oneYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.06 g of 3-amino-4-hydroxybenzoic acid in 20.6 ml of THF was added 4.81 g of CDI, followed by stirring at room temperature for 1 hour. The reaction mixture was added dropwise to a mixed liquid of 3.06 g of sodium borohydride in 20.6 ml of THF and 8.26 ml of water, cooled to 0° C., which had been separately prepared, followed by stirring overnight. 1 M hydrochloric acid was added thereto, followed by extracting with ethyl acetate, and washing with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 1.2 g of 5-(hydroxymethyl)-1,3-benzoxazol-2(3H)-one.

Workup

  1. temperaturecooled to 0° C.
  2. customwhich had been separately prepared
  3. stirringby stirring overnight
  4. extractionby extracting with ethyl acetate
  5. washwashing with a saturated aqueous sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d589d9a15ea74aedba94904c0b385220
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Linked notes

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