Water → Acetic acid-2-(3-cyanopropyl)-benzyl ester

HRID 1287358Notes

Reaction equation

HRID 1287358 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][CH2:6][CH2:7][C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[CH2:10][O:11][C:12](=[O:14])[CH3:13].O.CCOCC>CS(C)=O>[C:1]([CH2:5][CH2:6][CH2:7][C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[CH2:10][O:11][C:12](=[O:14])[CH3:13])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 20322157HCID 20322157, compound

Product 1

HCID 20322111Acetic acid-2-(3-cyanopropyl)-benzyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

With exclusion of humidity 12.5 g (0.25 mol) of dry NaCN were heated in 65 ml of anhydrous DMSO to 90°C and at this temperature 44.8 g (0.2 mol) of acetic acid-2-(3-chloropropyl)-benzyl ester were added dropwise. Then the mixture was heated for 50 minutes to 120°C and distributed after cooling between water and ether. The aqueous phase was extracted three times with ether, the organic phase was washed three times with a saturated sodium chloride solution, dried and concentrated under reduced pressure. The product boiled at 128°C/0.2 mm mercury.

Workup

  1. additionwere added dropwise
  2. temperatureThen the mixture was heated for 50 minutes to 120°C
  3. extractionThe aqueous phase was extracted three times with ether
  4. washthe organic phase was washed three times with a saturated sodium chloride solution
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-449eb57bd4f24927ba7cb0794151f083
Source dataset
uspto-grants-1976_10
Patent number
US03984459

Reaction notes

Loading…