Hydrochloric Acid → HCID 58240634, compound

HRID 1802832Notes

Reaction equation

HRID 1802832 reaction equation
C([O:4][C:5]12[CH:11]3[C:12]([CH3:18])([CH3:17])[CH:13]4[CH2:16][C:10]3([CH2:15][CH2:14]4)[C:9]([CH3:20])([CH3:19])[CH2:8][CH:7]1[O:6]2)(=O)C.[OH-].[Na+].Cl>O.C(O)C>[OH:4][CH:5]1[CH:11]2[C:12]([CH3:17])([CH3:18])[CH:13]3[CH2:16][C:10]2([CH2:15][CH2:14]3)[C:9]([CH3:20])([CH3:19])[CH2:8][C:7]1=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58240633HCID 58240633, compound

Product 1

HCID 58240634HCID 58240634, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,2,8,8-Tetramethyl-5-oxatetracyclo[7.2.1.01.7.04.6]dodec-6-yl acetate (3, 14.5 g, 61% pure, 0.032 mol) was added at r. t. to a solution of sodium hydroxide (30 g, 0.75 mol) in water (0.75 l) and ethanol (0.75 l). After overnight stirring at r. t., the reaction mixture was neutralized to pH 7 with 2M aqueous HCl solution and extracted with MTBE (2×0.5 l). The combined organic phases were washed with water (2×0.2 l), dried (Na2SO4) and concentrated in vacuo to give crude 5-hydroxy-2,2,7,7-tetramethyltricyclo[6.2.1.01.6]undecan-4-one (4, 13 g, colourless oil, partly solidifying on standing) which was used without further purification in the next steps. Besides two isomeric hydroxyketones, the mixture contained tautomeric forms of the oxidised 4 (diketone).

Workup

  1. extractionextracted with MTBE (2×0.5 l)
  2. washThe combined organic phases were washed with water (2×0.2 l)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acf9506c2bc04585b7262426bac54bcc
Source dataset
uspto-grants-2013_01
Patent number
US08349890B2

Reaction notes

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