Hydrochloric Acid → HCID 86706690, compound

HRID 1468078Notes

Reaction equation

HRID 1468078 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]3)[C:8]2=[O:11])=[CH:4][C:3]=1[CH3:18].CC(O)C.[OH-].[Na+].Cl>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]3)[C:8]2=[O:11])=[CH:4][C:3]=1[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 86706689HCID 86706689, compound2×

Product 1

HCID 86706690HCID 86706690, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

6′-Bromo-5′-methylspiro[cyclohexane-1,2′-indene]-1′,4(3′H)-dione (Intermediate 2, 1.38 g, 4.49 mmol) and propan-2-ol (16.6 mL, 215 mmol) were heated to 75° C. Ground NaOH (0.176 g, 4.40 mmol) was added. The resulting mixture was heated at reflux for 1.5 h and was then allowed to cool to r.t. The mixture was concentrated to half the volume and then water (15 mL) and toluene (15 mL) were added together with 6 M aq. HCl (0.749 mL, 4.49 mmol). The layers were separated and the aqueous layer was re-extracted with toluene (15 mL). The combined organic layers were dried over Na2SO4, concentrated and dried in vacuo to afford 1.36 g (98% yield) of the title compound as a mixture of isomers (˜70:30 mixture of isomers with the hydroxyl group in equatorial and axial position) and this mixture was used in the next step without further purification: MS (ES+) m/z 308, 311 [M+H]+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1.5 h
  3. concentrationThe mixture was concentrated to half the volume
  4. customThe layers were separated
  5. extractionthe aqueous layer was re-extracted with toluene (15 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-478ac2f7c7ae4c7cb9ba8c4d11f4446b
Source dataset
uspto-grants-2015_04
Patent number
US09000183B2

Reaction notes

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