Hydrochloric Acid → HCID 10268079, compound

HRID 1047357Notes

Reaction equation

HRID 1047357 reaction equation
[OH-].[Na+].[CH:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[C:4]31[O:16][O:15][C:14]1([CH2:21][CH2:20][CH:19]([CH2:22][C:23]([O-:25])=[O:24])[CH2:18][CH2:17]1)[O:13]3)[CH2:10]2.Cl>O.C(O)C>[CH:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[C:4]31[O:16][O:15][C:14]1([CH2:21][CH2:20][CH:19]([CH2:22][C:23]([OH:25])=[O:24])[CH2:18][CH2:17]1)[O:13]3)[CH2:10]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86653817HCID 86653817, compound

Product 1

HCID 10268079HCID 10268079, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydroxide (3.86 g, 96.57 mmol, 3 equiv.) in water (80 mL) was added to a solution of methyl (1 s, 4 s)-dispiro[cyclohexane-1,3′-[1,2,4]trioxolane-5′,2″-tricyclo[3.3.1.13,7]decan]-4-ylacetate (example 3) (10.83 g, 32.19 mmol, 1 equiv.) in 95% ethanol (150 mL). The mixture was stirred at 50° C. for about 4 h, cooled to 0° C., and treated with 1M hydrochloric acid (129 ml, 4 equiv). The precipitate was collected by filtration, washed with 50% aqueous ethanol (150 mL) and dried in vacuum at 40° C. to give the title compound as colorless solid. Yield: 9.952 g, 96%, mp: 146-148° C. (95% ethanol), 1HNMR (500 Hz, CDCl3): δ 1.19-1.41 (m, 2H), 1.60-2.05 (m, 21H), 2.27 (d, J=6.8 Hz, 2H).

Workup

  1. temperaturecooled to 0° C.
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with 50% aqueous ethanol (150 mL)
  4. customdried in vacuum at 40° C.

Sources & evidence

ORD record
ord-d2f8079a37aa4e98a13a5e8775b3edf7
Source dataset
uspto-grants-2013_10
Patent number
US08569519B2

Reaction notes

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