Hydrochloric Acid → HCID 13886164, compound

HRID 2166587Notes

Reaction equation

HRID 2166587 reaction equation
BrCCCC1CCCCCCCCCCC1=O.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].[OH:29][CH2:30][CH2:31][CH2:32][CH:33]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][C:34]1=[O:45].Cl>N1C=CC=CC=1>[C:24]1([CH3:25])[CH:26]=[CH:27][C:21]([S:18]([O:29][CH2:30][CH2:31][CH2:32][CH:33]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][C:34]2=[O:45])(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 101309872-(3-hydroxypropyl)cyclododecanoneHCID 149161932-(3-Bromopropyl)cyclododecan-1-one

Product 1

HCID 13886164HCID 13886164, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(3-Bromo-prop-1-yl)-cyclododecanone used hereinabove as starting material was prepared as follows: (a) 171.5 g (0.90 mole) of tosyl chloride were added under good stirring to a solution of 206.7 g (0.86 mole) of 2-(3-hydroxy-prop-1-yl)-cyclododecanone in 280 ml of pyridine cooled to 0°. After stirring at 0° to 10° for 3 further hours, the reaction mixture was kept overnight at 4°, then poured onto crushed ice and finally acidified with 600 ml of 36% aqueous HCl. After extraction with ether, drying of the organic layer over CaCl2 and evaporation, there were isolated 273 g (81% yield) of 2-(3-p-toluene-sulfonyloxy-prop-1-yl)-cyclododecanone.

Workup

  1. customwas prepared
  2. temperaturecooled to 0°
  3. additionpoured
  4. customonto crushed ice
  5. extractionAfter extraction with ether
  6. dry with materialdrying of the organic layer over CaCl2 and evaporation

Sources & evidence

ORD record
ord-25a68a21433149dc9b31f3d02fbed521
Source dataset
uspto-grants-1983_06
Patent number
US04387250

Reaction notes

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