Hydrochloric Acid → Toluene-4-sulfonic acid 2-cyano-2-phenylheptyl ester

HRID 333434Notes

Reaction equation

HRID 333434 reaction equation
[OH:1][CH2:2][C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:4]#[N:5].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C.Cl>ClCCl>[C:4]([C:3]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:2][O:1][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 669878522-Hydroxymethyl-2-phenylheptanenitrile

Product 1

HCID 86659207Toluene-4-sulfonic acid 2-cyano-2-phenylheptyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 4.24 g (19.5 mmol) of 2-hydroxymethyl-2-phenyl-heptanenitrile in 25 mL of dichloromethane are added 4.1 g (21.5 mmol) of p-toluenesulfonyl chloride and 6 mL of triethylamine. The reaction medium is stirred for 15 hours at room temperature and then treated with 1N hydrochloric acid solution and extracted with dichloromethane. The organic phase is dried over sodium sulfate, filtered and evaporated under pressure. A yellow oil is obtained and precipitated from a 9/1 heptane/diisopropyl ether mixture. The precipitate formed is filtered off and rinsed with diisopropyl ether. 5.26 g in the form of a beige-coloured powder are obtained in a yield of 72%.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under pressure
  5. customA yellow oil is obtained
  6. customprecipitated from a 9/1 heptane/diisopropyl ether mixture
  7. customThe precipitate formed
  8. filtrationis filtered off
  9. washrinsed with diisopropyl ether
  10. custom5.26 g in the form of a beige-coloured powder are obtained in a yield of 72%

Sources & evidence

ORD record
ord-7d8e6c08e21b4ed1b5afb236d2d8772b
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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