2-Methylbenzenesulfonic acid → HCID 10923041, compound

HRID 840064Notes

Reaction equation

HRID 840064 reaction equation
C1(C)C(S(O)(=O)=O)=CC=CC=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19].[CH:20]([O:22][CH2:23][CH3:24])=[CH2:21]>CCOCC>[CH2:20]([O:22][CH:23]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][Br:12])[CH3:24])[CH3:21]

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 8023Ethyl vinyl etherHCID 779706-Bromo-1-hexanol

Product 1

HCID 10923041HCID 10923041, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a cooled solution of 80 mg of toluenesulfonic acid in 40 ml of ether was fed 20 g (110 mmol) of 6-bromohexanol and 40 ml of ethyl vinyl ether simultaneously by separate additional funnels. The temperature of the reaction mixture was kept at 7° C. or lower during the feeds, which took 1 hour. The reaction mixture was stirred 20 minutes longer, then roughly 1 ml of triethylamine was added. The reaction mixture was washed with water and brine, dried over potassium carbonate, filtered and stripped to give 25.7 g of a pale yellow liquid, which was used without further purification.

Workup

  1. customby separate additional funnels
  2. customwas kept at 7° C.
  3. additionroughly 1 ml of triethylamine was added
  4. washThe reaction mixture was washed with water and brine
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-591c26b7090e49beb4911d15a8748707
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

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