Water → HCID 178448154, compound

HRID 1376295Notes

Reaction equation

HRID 1376295 reaction equation
[F:1][C:2]1[CH2:7][CH2:6][CH:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH:14]=[O:15])[CH2:10][CH2:9]2)[CH2:4][CH:3]=1.[CH2:16]([CH:19]([CH2:22]O)[CH2:20][OH:21])[CH2:17][CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH2:7][CH2:6][CH:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C@H:14]3[O:21][CH2:20][C@H:19]([CH2:16][CH2:17][CH3:18])[CH2:22][O:15]3)[CH2:10][CH2:9]2)[CH2:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 70211562-propylpropane-1,3-diolHCID 178520925HCID 178520925, compound

Product 1

HCID 178448154HCID 178448154, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

500 mg of trans-4-(4-fluoro-cyclohex-3-enyl)cyclohexanecarbaldehyde, 310 mg of 2-propyl-propane-l,3-diol and 50 mg of p-toluenesulphonic acid in 8 ml of toluene were boiled at reflux for 1 hour in an apparatus which was gassed with nitrogen and which was fitted with a water separator. After cooling the reaction solution was partitioned in water/ether. The organic phase was washed twice with water. The aqueous phases were extracted twice with ether. The organic phases were combined, dried over magnesium sulphate, filtered and the filtrate was evaporated. The crude product was recrystallized several times from ethanol/1% ethyl acetate and gave 350 mg of trans-2-[trans-4-(4-fluoro-cyclohex-3-enyl)cyclohexyl]-5-propyl-[1,3]-dioxane, m.p. (C-N)<room temperature; S-N 104° C., c1.p. (N-I) 118.3° C.;

Workup

  1. temperatureat reflux for 1 hour in an apparatus which
  2. temperatureAfter cooling the reaction solution
  3. customwas partitioned in water/ether
  4. washThe organic phase was washed twice with water
  5. extractionThe aqueous phases were extracted twice with ether
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe filtrate was evaporated
  9. customThe crude product was recrystallized several times from ethanol/1% ethyl acetate

Sources & evidence

ORD record
ord-ca1564c8f1964cb4be4d5e39e690326b
Source dataset
uspto-grants-1997_09
Patent number
US05662829

Reaction notes

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