Iodine → 1-(4-Chlorophenyl)-4-[2-(1,4-dioxa-spiro[4,5]decyl)ethyl]cyclohexanol

HRID 486358Notes

Reaction equation

HRID 486358 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.O=C1CCC(CC[CH:21]2[CH2:30][CH2:29][C:24]3([O:28][CH2:27][CH2:26][O:25]3)[CH2:23][CH2:22]2)CC1.[CH2:31](C1C=CC(O)=CC=1)[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1.O=C1CCC(C2CCC3(OCCO3)CC2)CC1.[Cl-].[NH4+]>O1CCCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:36]2([OH:39])[CH2:37][CH2:38][CH:33]([CH2:32][CH2:31][CH:27]3[CH2:26][O:25][C:24]4([CH2:23][CH2:22][CH2:21][CH2:30][CH2:29]4)[O:28]3)[CH2:34][CH2:35]2)=[CH:6][CH:7]=1

Participants

9

Reactant 7

HCID 807IodineHCID 7806p-BromochlorobenzeneHCID 25517Ammonium ChlorideHCID 801521,2-Bis(4-hydroxyphenyl)ethaneHCID 8109134-(1,4-Dioxa-spiro(4.5)dec-8-yl)-cyclohexanoneHCID 5462224MagnesiumHCID 102362768-[2-(4-Oxocyclohexyl)ethyl]-1,4-dioxaspiro[4,5]decane

Product 1

HCID 190948991-(4-Chlorophenyl)-4-[2-(1,4-dioxa-spiro[4,5]decyl)ethyl]cyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

4.53 g of magnesium shavings and a granule of iodine are treated with 150 ml of tetrahydrofuran while stirring and gassing with nitrogen. Subsequently, the mixture is treated dropwise within 20 minutes with a solution of 38.4 g of 1-bromo-4-chlorobenzene in 150 ml of tetrahydrofuran and boiled at reflux for 1.25 hours. Thereafter, the reaction mixture is cooled to 0° C. and treated dropwise at 0°-5° C. within 30 minutes with a solution of 35.7 g of 8-[2-(4-oxocyclohexyl)ethyl]-1,4-dioxaspiro[4,5]decane (prepared starting from 4,4'-(1,2-ethane-diyl)bisphenol in analogy to the synthesis of 8-(4-oxocyclohexyl)-1,4-dioxaspiro[4,5]decane described in EP-A-310,067) in 240 ml of tetrahydrofuran. The reaction mixture is stirred without cooling for a further 4 hours, then treated within 10 minutes with 240 ml of 10 percent ammonium chloride solution and extracted with diethyl ether. The ether phases are washed with water, dried over sodium sulphate, filtered and concentrated, there being obtained 1-(4-chlorophenyl)-4-[2-(1,4-dioxa-spiro[4,5]decyl)ethyl]cyclohexanol.

Workup

  1. temperatureat reflux for 1.25 hours
  2. customprepared
  3. stirringThe reaction mixture is stirred
  4. temperaturewithout cooling for a further 4 hours
  5. extractionextracted with diethyl ether
  6. washThe ether phases are washed with water
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-68b34dba3dec4ba5bc977f212e9defd8
Source dataset
uspto-grants-1994_03
Patent number
US05292452

Reaction notes

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