Benzenesulfonyl chloride → Undecan-5-one

HRID 637604Notes

Reaction equation

HRID 637604 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)C1=NO)[CH2:8]2.[C:13]1(S(Cl)(=O)=O)C=CC=C[CH:14]=1.[OH-:23].[Na+]>>[CH3:13][CH2:14][CH2:6][CH2:5][C:10](=[O:23])[CH2:1][CH2:8][CH2:7][CH2:9][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 64158Tricyclo[3.3.1.1(3,7)-]decanone, oxime

Product 1

HCID 98677Undecan-5-one

Conditions

Temperature
55 °C

Procedure

To a suspension of 3 grams (18 mmol) of 2-adamantanone oxime in 36 ml of 20% aqueous sodium hydroxide were added 5 grams (28 mmol) of benzenesulfonyl chloride with vigorous stirring at a temperature of 20°-30° C. The temperature was maintained below 30° C. until the exothermic reaction ceased, then raised to 55° C. and held there for 2 hours. The reaction mixture was worked up leaving 2 grams of 4-azatricyclo[4.3.1.13,8 ]undecan-5-one as white crystals melting at 306°-308° C. (recrystallized from hexane).

Workup

  1. temperatureThe temperature was maintained below 30° C. until the exothermic reaction
  2. customThe reaction mixture was worked up leaving
  3. custom2 grams of 4-azatricyclo[4.3.1.13,8 ]undecan-5-one as white crystals melting at 306°-308° C. (recrystallized from hexane)

Sources & evidence

ORD record
ord-3db2fd0bf404468592799dea13b06acb
Source dataset
uspto-grants-1985_12
Patent number
US04557865

Reaction notes

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