(-)-Mandelic acid → Mandelic Acid

HRID 1660490Notes

Reaction equation

HRID 1660490 reaction equation
[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].NC1CCC2C(=CC=C(OC)C=2)C1>CO>[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

4

Reactant 2

HCID 11914(-)-Mandelic acidHCID 199076-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine

Product 1

HCID 1292Mandelic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

47 of D-(-)-mandelic acid, dissolved in 650 ml of methanol, are added dropwise, whilst stirring, to a solution of 55 g of 2-amino-1,2,3,4-tetrahydro-6-methoxy-naphthalene in 650 ml of methanol. The reaction solution so obtained is left to stand for 3 hours at room temperature, the precipitated crystals filtered off, washed with ether and dried. The (-)-mandelic acid salt thus obtained, is recrystallised from hot methanol and the procedure repeated until, at any given time a test showed that the optical rotation of the amine set free from the mandelic acid salt by extraction with IN sodium carbonate solution/methylene chloride is constant. The (+)-antipode of the title compound thus obtained is converted to the hydrochloride and recrystallised from methanol. M.P. 262°-264°. [α]D20 =+77.6° (C=1 in methanol). [Hydrochloride salt form].

Workup

  1. additionare added dropwise
  2. customThe reaction solution so obtained
  3. waitis left
  4. filtrationthe precipitated crystals filtered off
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-5f153b0e819e429f8dfad874d994fc48
Source dataset
uspto-grants-1981_12
Patent number
US04308266

Reaction notes

Loading…