Cinchonidine → 2-(6-Methoxy-2-naphthyl)propionic acid

HRID 1414674Notes

Reaction equation

HRID 1414674 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](C1C3C(=CC=CC=3)C=CC=1)([CH3:17])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2.C=C[C@@H]1[C@@H]2C[C@@H]([C@H](O)C3C=CN=C4C=CC=CC=34)N(CC2)C1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 101744CinchonidineHCID 86734387HCID 86734387, compound

Product 1

HCID 13022-(6-Methoxy-2-naphthyl)propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.3 g. of 6-methoxy-2-naphthyl-α-naphthyl-α-methylacetic acid, 2.9 g. of cinchonidine, and 50 ml. of methanol is stirred for two hours; the mixture is then allowed to stand until crystallization is complete. The crystals are filtered off and washed with methanol. The crystals are recrystallized from methanol, filtered, washed, and dried. The pure crystals are added to 60 ml. of 0.2N hydrochloric acid. The resulting mixture is stirred for two hours and then extracted with diethyl ether. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, and evaporated to yield one of the optical isomers of 6-methoxy-2-naphthyl-α-methylacetic acid. The filtrates from the above filtrations are acidified with aqueous dilute hydrochloric acid and the product is isolated by diethyl ether extractions to give the other optical isomer of 6-methoxy-2-naphthyl-α-methylacetic acid.

Workup

  1. additionA mixture of 2.3 g
  2. customto stand until crystallization
  3. filtrationThe crystals are filtered off
  4. washwashed with methanol
  5. customThe crystals are recrystallized from methanol
  6. filtrationfiltered
  7. washwashed
  8. customdried
  9. additionThe pure crystals are added to 60 ml
  10. extractionextracted with diethyl ether
  11. washwashed with water to neutrality
  12. dry with materialdried over sodium sulfate
  13. customevaporated

Sources & evidence

ORD record
ord-07030ffb3e3341cc91834bc37f4b38e3
Source dataset
uspto-grants-1977_01
Patent number
US04001301

Reaction notes

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