Ethyl benzoylacetate → HCID 20200616, compound

HRID 979541Notes

Reaction equation

HRID 979541 reaction equation
[O-]CC.[Na+].[C:5]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH2:28][CH2:29][Cl:30]>C(O)C.CCOCC.O>[C:5]([CH:13]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH2:28][CH2:29][Cl:30])[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 2723922Sodium ethoxideHCID 123739901-(Chloromethyl)-2-(3-chloropropyl)benzene

Product 1

HCID 20200616HCID 20200616, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of sodium ethoxide (from 0.53 g. sodium) in ethanol (80 ml.) was treated with ethyl benzoylacetate (4.42 g.). After 1 hour, -(o-chloromethylphenyl)propyl chloride (4.57 g.) was added and stirring was continued for 24 hours. The mixture was then diluted with ether (100 ml.) and water (100 ml.). The organic layer was separated, washed with saturated brine (50 ml.), dried (MgSO4) and evaporated to give ethyl 2-benzoyl-3-(o-(3-chloropropyl)phenyl]propanoate (A) as a yellow oil (7.66 g.), NMR: 1.1 (3H,t), 2.1 (2H,m), 2.7-3.7 (6H,m), 4.1 (2H,m), 4.65 (1H,t) and 7.0-8.2 (9H,m)ppm, which was used without further purification.

Workup

  1. waitwas continued for 24 hours
  2. customThe organic layer was separated
  3. washwashed with saturated brine (50 ml.)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-243576552d244c86b7b48fc100e7caff
Source dataset
uspto-grants-1987_05
Patent number
US04668698

Reaction notes

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