(-)-2-amino-1butanol D-(-)-mandelate → (-)-Mandelic acid

HRID 443614Notes

Reaction equation

HRID 443614 reaction equation
[C:1]([O:11]CC(N)CC)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]>O>[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

3

Reactant 1

HCID 70562055(-)-2-amino-1butanol D-(-)-mandelate

Product 1

HCID 11914(-)-Mandelic acidYield 87.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A portion of the (-)-2-amino-1butanol D-(-)-mandelate wet cake 155 grams "as is" -90.3% pure; 0.58 mole) from resolution A is dissolved in the mother liquor plus water washes from (D) at 50°-55° C. and the solution is distilled under vacuum to remove 41 mls of methanol and water. The concentrated solution is then treated with 37% hydrochloric acid (60 mls) and processed as described in (D) to obtain 77 grams of D-(-)-mandelic acid (87.4% of theoretical; m.p. 130°-132° C.; [α]D25° =-152.9° (C=2, H2O)).

Workup

  1. distillationthe solution is distilled under vacuum
  2. customto remove 41 mls of methanol and water
  3. additionThe concentrated solution is then treated with 37% hydrochloric acid (60 mls)

Sources & evidence

ORD record
ord-218b2a9af3d84727a8736cee0021b3e7
Source dataset
uspto-grants-1981_04
Patent number
US04260815

Reaction notes

Loading…