Hydrochloric Acid → 1-Decyn-4-ol

HRID 259986Notes

Reaction equation

HRID 259986 reaction equation
Cl[C:2](=[CH2:12])[CH2:3][CH:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[OH:5].[OH-].[Na+].Cl>CN(C)C=O>[CH2:6]([CH:4]([CH2:3][C:2]#[CH:12])[OH:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11030613HCID 11030613, compound

Product 1

HCID 5441861-Decyn-4-olYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20.00 Grams of the 2-chloroallyl-n-hexylcarbinol obtained above were dissolved in 200 g of N,N-dimethylformamide, and 8.39 g of sodium hydroxide in a flake form were added. The resultant mixture was stirred at 25° C. for 10 hours. After the reaction was completed, the reaction mixture was neutralized with concentrated hydrochloric acid, and insolubles were filtered off. After the filtrate was concentrated under reduced pressure, the concentration residue was subjected to extraction with toluene, washed with a 7% sodium carbonate aqueous solution and then dried over sodium sulfate. The desiccant was filtered off, and the toluene was distilled off. The resultant oily substance was distilled under reduced pressure to give 15.70 g of n-hexylpropargylcarbinol. The results were as follows.

Workup

  1. filtrationwere filtered off
  2. concentrationAfter the filtrate was concentrated under reduced pressure
  3. extractionthe concentration residue was subjected to extraction with toluene
  4. washwashed with a 7% sodium carbonate aqueous solution
  5. dry with materialdried over sodium sulfate
  6. filtrationThe desiccant was filtered off
  7. distillationthe toluene was distilled off
  8. distillationThe resultant oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-5805fdc2f421441ba9abb78e51203eec
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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