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

HRID 486358ノート

反応式

HRID 486358 の反応式
[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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-68b34dba3dec4ba5bc977f212e9defd8
出典データセット
uspto-grants-1994_03
特許番号
US05292452

反応ノート

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