Sodium Hydroxide → 2-Aminobenzyl alcohol

HRID 1155331

Reaction equation

HRID 1155331 reaction equation
O=C1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[CH2:4][O:3]1.[OH-].[Na+]>C(OC(C)C)(=O)C.O>[NH2:7][C:6]1[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=1[CH2:4][OH:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 257861,4-Dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 214392-Aminobenzyl alcohol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7915Isopropyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

The reaction mixture from Stage A was boiled so as to drive off the isopropyl acetate solvent. A solution of 100 g of sodium hydroxide in 100 ml of water was added to the residue, and the whole was refluxed for 2 hours. After cooling to 45° C., the product was extracted with four 270 ml portions of isopropyl acetate. The isopropyl acetate was then distilled off and the product recrystallized from toluene to give 100 g (63% of theoretical) of 97-98% pure 2-amino-benzyl alcohol; m.p. 83°-83.5° C.

Workup

  1. temperaturethe whole was refluxed for 2 hours
  2. extractionthe product was extracted with four 270 ml portions of isopropyl acetate
  3. distillationThe isopropyl acetate was then distilled off
  4. customthe product recrystallized from toluene

Sources & evidence

ORD record
ord-caa27b79386f449a895ea5d3d2f83872
Source dataset
uspto-grants-1981_11
Patent number
US04301283

Linked notes

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