Acetic Anhydride → HCID 86705070, compound

HRID 2176057Notes

Reaction equation

HRID 2176057 reaction equation
[CH3:1][C:2]([OH:9])([CH3:8])[C:3]#[C:4][CH2:5][CH2:6][OH:7].[C:10](OC(=O)C)(=[O:12])[CH3:11].C(N(CC)CC)C>ClCCl>[C:10]([O:7][CH2:6][CH2:5][C:4]#[C:3][C:2]([OH:9])([CH3:8])[CH3:1])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86705071HCID 86705071, compound

Product 1

HCID 86705070HCID 86705070, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

100 g (0.78 mol) of 5-methylhex-3-yne-1,5-diol were dissolved in 800 ml of dichloromethane and cooled to 0° C. 113 ml (1.11 mol) of acetic anhydride were added in one portion. 127 ml (1.25 mol) of triethylamine were cooled to 0-2° C. and added within 20 min. The reaction mixture was stirred at 0° C. for 2 h. The cooling was removed and the reaction mixture was stirred a 20° C. for 16 h. The mixture was cooled to 0° C. and 1200 ml of a 5% hydrochloric acid solution were added, in the course of which the temperature of the reaction mixture was kept below 5° C. The mixture was extracted three times with 150 ml each time of tert-butyl methyl ether (MTBE), and the combined organic phases were stirred four times with 400 ml each time of 5% aqueous sodium hydrogen carbonate solution for 1 h each time, until no further evolution of gas was observable in each case. The organic phase was washed with 1 l of demineralized water and dried over sodium sulfate, and the solvent was removed. This gave 122.21 g (yield 92%) of a clear, dark yellow liquid. The purity was determined by gas chromatography to be 99.5%.

Workup

  1. additionadded within 20 min
  2. customThe cooling was removed
  3. stirringthe reaction mixture was stirred a 20° C. for 16 h
  4. temperatureThe mixture was cooled to 0° C.
  5. addition1200 ml of a 5% hydrochloric acid solution were added, in the course of which the temperature of the reaction mixture
  6. customwas kept below 5° C
  7. extractionThe mixture was extracted three times with 150 ml each time of tert-butyl methyl ether (MTBE)
  8. stirringthe combined organic phases were stirred four times with 400 ml each time of 5% aqueous sodium hydrogen carbonate solution for 1 h each time
  9. washThe organic phase was washed with 1 l of demineralized water
  10. dry with materialdried over sodium sulfate
  11. customthe solvent was removed

Sources & evidence

ORD record
ord-d29074b8f55c48e082e2e6edc85d71cc
Source dataset
uspto-grants-2015_06
Patent number
US09062136B2

Reaction notes

Loading…