1,1-Dichloroethane → 2-(4-Dodecanoylphenyl)ethyl acetate

HRID 1451620Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:7])[CH3:6].[C:17](Cl)(=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].Cl[CH:31](Cl)C>>[C:5]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:31])=[CH:13][CH:12]=1)(=[O:7])[CH3:6]

Participants

Reactant 4

HCID 63651,1-Dichloroethane

HCID 76542-Phenylethyl Acetate

HCID 87287Undecanoyl chloride

HCID 6451240Aluminum(III) Chloride

Product 1

HCID 218493882-(4-Dodecanoylphenyl)ethyl acetate

Procedure

Aluminum chloride (48.2 g) was added to dichloroethane (400ml) in a stream of nitrogen and the mixture was stirred at room temperature. Then, phenethyl acetate (39.6 g) and undecanoyl chloride (52.7 g) were dropwise added thereto under ice-cooling and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue obtained was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20) to give the subject compound (34.5 g) as pale yellow crystals.

Workup

temperatureunder ice-cooling
stirringthe mixture was stirred at room temperature overnight
extractionextracted with diethyl ether
washThe ether layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was distilled away
customthe residue obtained
customwas purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20)

Sources & evidence

ORD record: ord-82f82add16fb405faa8ef68a2edc734e
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05604229

Reaction notes

Loading…