Acetic Acid → 1-Phenyl-3-acetoxybutane

HRID 1938103Notes

Reaction equation

HRID 1938103 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]([OH:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[C:19](O)(=[O:21])[CH3:20].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:19]([O:11][CH:9]([CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:10])(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 1140TolueneHCID 613024-Phenyl-2-butanol

Product 1

HCID 615171-Phenyl-3-acetoxybutaneYield 98.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Into a four-necked flask provided with a thermometer and a stirrer, 150 g (1 mol) of 4-phenyl-2-butanol (XXX-35), 500 ml of toluene and 200 ml of pyridine were charged. 122.4 g (1.2 mol) of anhydrous acetic acid and 1 g of 4-dimethylaminopyridine were further added thereto to react them for 4 hours, while temperature being maintained at 40°-50° C. After completion of the reaction, the reaction mixture was poured into 500 ml of 4N hydrochloric acid solution, extracted and fractionated, and then an organic layer was washed with 1N hydrochloric acid, water, 5% sodium bicarbonate solution and water in the order. The thus-obtained organic layer was concentrated under a reduced pressure to obtain 189 g of 2-acetoxy-4-phenylbutane (XXIX-35) with yield of 98.5%.

Workup

  1. additionwere charged
  2. customto react them for 4 hours
  3. temperaturewhile temperature being maintained at 40°-50° C
  4. customAfter completion of the reaction
  5. extractionextracted
  6. washan organic layer was washed with 1N hydrochloric acid, water, 5% sodium bicarbonate solution and water in the order
  7. concentrationThe thus-obtained organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-c8c37081e6e1451cb431d8c9170b5a46
Source dataset
uspto-grants-1997_12
Patent number
US05693251

Reaction notes

Loading…