Water → HCID 13711959, compound

HRID 894473Notes

Reaction equation

HRID 894473 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([O:16][CH:17]([CH2:38][CH2:39][C:40]([CH3:42])=[CH2:41])[CH:18]([CH3:37])[CH2:19][CH2:20][CH2:21][C:22]1([CH3:36])[CH:28]2[O:29][C:25]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])([CH2:26][CH2:27]2)[CH2:24][O:23]1)(=[O:15])[CH3:14].C([O-])(O)=O.[Na+].O>C1C=CC=CC=1.CCOCC>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][C:25]12[O:29][CH:28]([CH2:27][CH2:26]1)[C:22]([CH2:21][CH2:20][CH2:19][CH:18]([CH3:37])[CH:17]([O:16][C:13](=[O:15])[CH3:14])[CH2:38][CH:39]=[C:40]([CH3:42])[CH3:41])([CH3:36])[O:23][CH2:24]2)[CH3:35]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 13135986HCID 13135986, compound

Product 1

HCID 13711959HCID 13711959, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
130 °C

Procedure

p-Toluenesulfonic acid monohydrate (8.2 mg) is added to benzene (12 ml). The mixture is stirred and refluxed in a Dean-Stark apparatus and some of the benzene (4 ml) is drained from the side-arm. The bicyclic acetoxy ester, ethyl(1RS,4SR,5RS)-4-(5-acetoxy-4,8-dimethyl-8-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetate (85 mg, 0.2 mM), dissolved in benzene (6 ml), is added at room temperature to the above mixture and the resultant mixture is stirred and refluxed (bath at 130° C.) for two hours. The temperature of the heating bath is then lowered to 90° C. and the stirring is continued at 90° C. for sixteen hours and then at room temperature for seventy-two hours. The reaction mixture is added to saturated NaHCO3 --H2O (10 ml) and ether (20 ml). The organic layer is separated, washed with saturated NaCl--H2O, dried with Na2SO4, filtered, and evaporated in vacuo to give ethyl(1RS, 4SR,5RS)-4-(5-acetoxy-4,8-dimethyl-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetate (80.4 mg, 95%).

Workup

  1. temperaturerefluxed in a Dean-Stark apparatus
  2. additionis added at room temperature to the above mixture
  3. customis then lowered to 90° C.
  4. waitthe stirring is continued at 90° C. for sixteen hours
  5. waitat room temperature for seventy-two hours
  6. customThe organic layer is separated
  7. washwashed with saturated NaCl--H2O
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-4358ee45f6034c8d8c10442cb8746e3a
Source dataset
uspto-grants-1981_08
Patent number
US04284565

Reaction notes

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