Water → HCID 54150769, compound

HRID 851807Notes

Reaction equation

HRID 851807 reaction equation
C1(S([CH2:10][CH2:11][CH2:12][CH:13]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=O)(=O)=O)C=CC=CC=1.CC(C)([O-])C.[K+].O.CCOCC>C1(C)C=CC=CC=1>[C:13]12[CH2:12][CH2:11][CH:10]=[C:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=2

Participants

6

Reactant 4

HCID 962Water2×HCID 3283Diethyl EtherHCID 205012032-[3-(Benzenesulfonyl)propyl]cyclododecan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 54150769HCID 54150769, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.728 g (2 mmole) of 2-(3-phenylsulfonyl-prop-1-yl)-cyclododecanone and 0.560 g (5 mmole) of potassium tert-butoxide in 8 ml of toluene were heated to reflux for 1 hour in a reaction vessel fitted with a water separator. After cooling to 10°, addition of water (15 ml), extraction with ether (2×15 ml), washing of the organic layer with brine (15 ml), then with water, drying over Na2SO4, evaporation and final distillation (0.02 Torr--bath temperature: 140°) there were isolated 0.340 g (83% yield) of the desired compound.

Workup

  1. temperatureto reflux for 1 hour in a reaction vessel
  2. temperatureAfter cooling to 10°
  3. washwashing of the organic layer with brine (15 ml)
  4. dry with materialwith water, drying over Na2SO4, evaporation
  5. distillationfinal distillation (0.02 Torr--bath temperature: 140°) there

Sources & evidence

ORD record
ord-9dc273c0e3794523a47d5776a1f17966
Source dataset
uspto-grants-1983_05
Patent number
US04386220

Reaction notes

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