Phenylacetyl chloride → HCID 21532238, compound

HRID 1657949Notes

Reaction equation

HRID 1657949 reaction equation
[CH2:1]([OH:10])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:11]1([CH2:17][C:18](Cl)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOCC>[C:11]1([CH2:17][C:18]([O:10][CH2:1]/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 53649412-Nonen-1-ol, (2E)-

Product 1

HCID 21532238HCID 21532238, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a flask equipped with a reflux condenser, mechanical stirrer and dropping funnel is added trans-2-nonenol (14.2 g, 0.1 mole), N1N-dimethylaniline (12 g, 0.1 mole) and 20 ml ether. To the stirred mixture is added dropwise phenylacetyl chloride (15.5 g, 0.1 mole) at a rate to maintain a vigorous reflux of ether. After the addition, the mixture is warmed on a water bath for 2 hours and then allowed to stand several hours. The ether layer is separated from the precipitate and extracted with 10% sulfuric acid. The ether layer is dried over anhydrous sodium sulfide and purified up to give trans-2-nonenyl phenylacetate.

Workup

  1. customTo a flask equipped with a reflux condenser, mechanical stirrer
  2. temperatureto maintain
  3. additionAfter the addition
  4. temperaturethe mixture is warmed on a water bath for 2 hours
  5. waitto stand several hours
  6. customThe ether layer is separated from the precipitate
  7. extractionextracted with 10% sulfuric acid
  8. dry with materialThe ether layer is dried over anhydrous sodium sulfide
  9. custompurified up

Sources & evidence

ORD record
ord-e22cccad6af0450a8cc1378d0456e7fd
Source dataset
uspto-grants-1976_06
Patent number
US03962321

Reaction notes

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