Hydrochloric Acid → HCID 12806953, compound

HRID 2058596Notes

Reaction equation

HRID 2058596 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([O:20][CH2:21][CH:22]2[CH2:26][O:25]C(C)(C)[O:23]2)=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:29][CH3:30])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:31])[CH:5]=1.Cl.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>CC(C)=O>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([O:20][CH2:21][CH:22]([OH:23])[CH2:26][OH:25])=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:29][CH3:30])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:31])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 12806952HCID 12806952, compound

Product 1

HCID 12806953HCID 12806953, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 165 mg of (2,2-dimethyl-1,3-dioxolan-4-yl)methyl [(5,6-dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetate from Example 109, Step A is dissolved in 100 ml. of 0.075 N hydrochloric acid and 20 ml. of acetone and heated, with stirring at 50°-55° C. for 2 hours. The mixture is cooled and neutralized with a solution of sodium bicarbonate. The solution is saturated with sodium chloride and extracted two times with 100 ml. portions of 20% tetrahydrofuran in ether. The extract is dried over Na2SO4. After filtration, the filtrate was concentrated to a yellow oil that solidified on standing. After recrystallization from tetrahydrofuran-ether-petroleum ether, there is obtained 110 mg. of product, m.p. 135°-138° C.

Workup

  1. dissolutionis dissolved in 100 ml
  2. temperatureThe mixture is cooled
  3. extractionextracted two times with 100 ml
  4. dry with materialThe extract is dried over Na2SO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated to a yellow oil that
  7. customAfter recrystallization from tetrahydrofuran-ether-petroleum ether
  8. customthere is obtained 110 mg

Sources & evidence

ORD record
ord-d4165861b7894d47b451f7d6586261fa
Source dataset
uspto-grants-1982_03
Patent number
US04317922

Reaction notes

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