Hydrochloric Acid → 3-Phenylbutyl acetate

HRID 1938107Notes

Reaction equation

HRID 1938107 reaction equation
[C:1]1([CH:7]([CH3:11])[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:19]([O:10][CH2:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:11])(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 7918Acetic AnhydrideHCID 94243Benzenepropanol, gamma-methyl-

Product 1

HCID 30164553-Phenylbutyl acetateYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Into a four-necked flask provided with a stirring means and a thermometer, 150 g (1 mol) of (+)-3-phenyl-1-butanol (XXVI-60), 500 ml of toluene and 200 ml of pyridine were charged, and 122.4 g (1.2 mol) of acetic acid anhydride and 1 g of 4-dimethylaminopyridine were further added thereto. The mixture was reacted 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, extracted and fractionated. The resulting organic layer was washed with 1N hydrochloric acid, water, 5% sodium bicarbonate aqueous solution ad water in the order. The thus-obtained organic layer was concentrated under a reduced pressure to obtain 190 g of (+)-1-acetoxy-3-phenylbutane (XXV-60) with yield of 99.0%.

Workup

  1. customInto a four-necked flask provided with a stirring means
  2. customThe mixture was reacted for 4 hours while temperature
  3. temperaturebeing maintained at 40°-50° C
  4. customAfter completion of the reaction
  5. extractionextracted
  6. washThe resulting organic layer was washed with 1N hydrochloric acid, water, 5% sodium bicarbonate aqueous solution ad water in the order
  7. concentrationThe thus-obtained organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-1e8c16cae6b446ad8147a8e06dbad788
Source dataset
uspto-grants-1997_12
Patent number
US05693251

Reaction notes

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