Hydrochloric Acid → HCID 13174739, compound

HRID 640809Notes

Reaction equation

HRID 640809 reaction equation
[CH:1]([O:3][CH2:4][CH3:5])=[O:2].C([O:8][C:9](=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)C.[H-].[Na+].Cl>C(OCC)C>[CH2:4]([O:3][C:1](=[O:2])[CH:10]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH:9]=[O:8])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 84177Ethyl (4-chlorophenyl)acetate

Product 1

HCID 13174739HCID 13174739, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl formate (7.46 g, 0.101 mol) was added dropwise to a stirred ice-cooled suspension of (4-chlorophenyl)acetic acid ethyl ester (20.0 g, 0.101 mol) and NaH (0.131 mol) in diethyl ether (100 mL). The mixture was then allowed to warm to room temperature overnight. The mixture neutralised (1 M HCl); the organic layer was isolated, dried, and the solvent removed to give 2-(4-chlorophenyl)-3-oxo-propanoic acid ethyl ester as a colourless solid (19.8 g, 87%). 1H NMR (CDCl3): δ 12.14 (d, J=12.8, 1H), 7.31-7.18 (m, 4H), 4.29 (q, J=7.2, 2H), 1.57 (br, 1H), 1.29 (t, J=7.2, 3H).

Workup

  1. temperaturecooled
  2. customthe organic layer was isolated
  3. customdried
  4. customthe solvent removed

Sources & evidence

ORD record
ord-9c68496a70834183bfc4ac8812e4bf27
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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