Benzyl Chloride → (Benzyloxy)cyclododecane

HRID 36467

反応式

HRID 36467 の反応式
[H-].[CH:2]1([OH:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:16]1([CH2:15][O:14][CH:2]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

4

反応物 3

HCID 7503Benzyl ChlorideHCID 15595CyclododecanolHCID 166653Hydride

生成物 1

HCID 15441422(Benzyloxy)cyclododecane

反応条件

温度
125 °C

実験手順

The hydride was mixed, under an argon atmosphere and by mechanical stirring, with cyclododecanol (130.0 g. 0.71 mol) and benzyl chloride (650.0 g, 5.14 mol). The reaction mixture was heated to 125° C. The mixture became very viscous when the temperature reached between 60° and 70° C. A mild exotherm was observed at about 100° C. which resulted in a marked viscosity decrease. If an efficient reflux condenser is not used, some external cooling may be necessary during the mild exotherm. The internal flask temperature increased to about 120° C. over ten minutes. The reaction flask was heated at 120° to 125° C. for an additional hour and then it was cooled to 25° C. The excess hydride was carefully destroyed by the addition of 100 mL of 95% ethanol under an argon atmosphere. The mixture was treated with 500 mL of aqueous saturated sodium chloride solution and extracted with three 400 mL portions of hexane. The organic layer was collected, washed with two 100 mL portions of water and two 100 mL portions of aqueous sodium chloride solution. The product mixture was dried over magnesium sulfate, filtered, and concentrated at 50° C. and 15 mm. The product was distilled at 144°-146° C./0.2 mm to give (180.7 g) 93.0% of the theoretical yield. Gas chromatography ("GC") showed that the product was 99% of a single component, IR (neat, cm-1) 2930, 2865, 1475, 1455, 1095 (C-O-C), 1070, 740; 13C NMR (ppm CDC13) 139.31, 128.17, 127.54, 127.21, 76.26 (α-ring carbon), 70.22 (α-chain carbon), 28.91, 24.75, 24.31, 23.30, 23.19, 20.81; MS, m/z (relative intensity) 274 (M+, 1.5), 245(0.1), 230(0.4), 183(8.2), 174(0.9),160(1.0), 145(0.8), 133(2.3), 118(2.7), 104(10.4), 91(100), 81(3.2), 65(12.7), 56(2.1). Anal calcd for C19H30O:C,83.15;H,11.02. Found: C,83.33;H,11.18.

後処理

  1. customreached between 60° and 70° C
  2. customwas observed at about 100° C.
  3. customresulted in a marked viscosity decrease
  4. customIf an efficient reflux condenser is not used
  5. temperaturesome external cooling may
  6. temperatureThe internal flask temperature increased to about 120° C. over ten minutes
  7. temperatureThe reaction flask was heated at 120° to 125° C. for an additional hour
  8. temperatureit was cooled to 25° C
  9. customThe excess hydride was carefully destroyed by the addition of 100 mL of 95% ethanol under an argon atmosphere
  10. additionThe mixture was treated with 500 mL of aqueous saturated sodium chloride solution
  11. extractionextracted with three 400 mL portions of hexane
  12. customThe organic layer was collected
  13. washwashed with two 100 mL portions of water and two 100 mL portions of aqueous sodium chloride solution
  14. dry with materialThe product mixture was dried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated at 50° C.
  17. distillationThe product was distilled at 144°-146° C./0.2 mm
  18. customto give (180.7 g) 93.0% of the theoretical yield

出典と根拠

ORDレコード
ord-d35ef523d7bd42f3a48e2be15cd50379
出典データセット
uspto-grants-1995_05
特許番号
US05414142

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