Isopropanol → 7-Tetradecynoic acid

HRID 1284440Notes

Reaction equation

HRID 1284440 reaction equation
[CH2:1]([OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C([OH:19])(C)C>CC(C)=O.OS(O)(=O)=O>[C:1]([OH:19])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 35630467-tetradecyn-1-ol

Product 1

HCID 53127097-Tetradecynoic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 7-tetradecyne-1-ol (2.10 g) in acetone (100 ml) was added dropwise to a vigorously stirred solution of 20 ml of 1M CrO3 in 10N H2SO4 cooled in ice. The addition took 30 hours after which 5 ml of isopropyl alcohol was added and the reaction mixture was filtered. The filtrate was diluted with 50 ml of water and extracted five times with ether. The combined organic phases were washed with water and saturated NaCl solution. The ether solution was then washed two times with 2N NaOH. The combined basic washes were extracted again with ether and acidified with 6 N HCl. Extraction with CHCl3 (3 times), drying (MgSO4) and removal of solvent under reduced pressure gave 1.95 g of 7-tetradecynoic acid as a yellow oil, which solidified on standing.

Workup

  1. temperaturecooled in ice
  2. additionThe addition
  3. filtrationthe reaction mixture was filtered
  4. additionThe filtrate was diluted with 50 ml of water
  5. extractionextracted five times with ether
  6. washThe combined organic phases were washed with water and saturated NaCl solution
  7. washThe ether solution was then washed two times with 2N NaOH
  8. extractionThe combined basic washes were extracted again with ether
  9. extractionExtraction with CHCl3 (3 times)
  10. customdrying
  11. custom(MgSO4) and removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-ae0292882f8e4111961e623a18ca2638
Source dataset
uspto-grants-1986_01
Patent number
US04563348

Reaction notes

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