Hydrochloric Acid → HCID 19710530, compound

HRID 726198Notes

Reaction equation

HRID 726198 reaction equation
CO.[CH3:3][O:4][C:5]1[C:6](=[O:17])[CH:7]2[CH:12]([C:13](=[O:15])[CH:14]=1)[CH:11]1[CH2:16][CH:8]2[CH:9]=[CH:10]1.C([O-])([O-])=O.[Na+].[Na+].Cl>C(Cl)(Cl)Cl>[CH3:3][O:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[CH:11]3[CH2:16][CH:8]([CH:9]=[CH:10]3)[C:7]=2[C:6]=1[OH:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 10340Sodium CarbonateHCID 13284018HCID 13284018, compound

Product 1

HCID 19710530HCID 19710530, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To stirred MeOH (65 mL), which had been purged with N2 for 5 min, there was added 1,4,4a,8a-tetrahydro-6-methoxy-1,4-methanonaphthalene-5,8-dione (47, 1.50 g, 7.30 mmol) to give a solution. Solid Na2CO3 (2.02 g, 14.6 mmol) was then added under N2. The resulting light green suspension was allowed to stir under N2 for 15 min at rt. TLC analysis (10% MeOH, 90% CHCl3) indicated total consumption of the organic starting material. While still under N2, the reaction was diluted with H2O (20 mL). The pH was adjusted to slightly acidic by the slow and careful addition of concd HCl, after which the solution was light pink. The methanol was then removed in vacuo (vacuum relieved with N2) to give a light green solution. The pH was approximately 8. The pH was then adjusted to 2 with 10% HCl at which point the product crystallized. The crystals were collected, washed with 10% HCl (4×3 mL) and dried in vacuo to yield 48 as a near colorless crystalline solid (1.32 g, 88%, pure by TLC and 1H NMR); mp 151°-153° C.; 1H NMR (vide infra).

Workup

  1. customhad been purged with N2 for 5 min
  2. customto give a solution
  3. customconsumption of the
  4. additionWhile still under N2, the reaction was diluted with H2O (20 mL)
  5. additioncareful addition of concd HCl
  6. customThe methanol was then removed in vacuo (vacuum relieved with N2)
  7. customto give a light green solution
  8. customcrystallized
  9. customThe crystals were collected
  10. washwashed with 10% HCl (4×3 mL)
  11. customdried in vacuo

Sources & evidence

ORD record
ord-337da1bfc19349af90f4f55c4013d81f
Source dataset
uspto-grants-1998_01
Patent number
US05708168

Reaction notes

Loading…