Ethanol → HCID 15346462, compound

HRID 550951Notes

Reaction equation

HRID 550951 reaction equation
[CH2:1]([CH:8]([C:14]([O:16]CC)=[O:15])[C:9]([O:11]CC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH2:21](O)[CH3:22]>>[CH2:21]([C:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]([OH:16])=[O:15])[C:9]([OH:11])=[O:10])[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 69090Diethyl 2-benzylpropanedioate

Product 1

HCID 15346462HCID 15346462, compound

Procedure

To a solution of diethyl benzylmalonate (20.0 g, 80 mmol) in ethanol (500 mL) was added potassium hydroxide (4.7 g, 84 mmol) as pellets. The mixture was stirred at room temperature for 24 h, and concentrated to dryness in vacuo. The residue was dissolved in water (300 mL), transferred to a separatory funnel, and washed with ether (2×150 mL). The aqueous solution was acidified to pH˜2 by adding conc. HCl, and extracted with ether (2×400 mL). The organic layer was dried over MgSO4, filtered and evaporated to dryness in vacuo, yielding the title compound as an oil residue (16.9 g, 95%) which was used without further purification.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. dissolutionThe residue was dissolved in water (300 mL)
  3. customtransferred to a separatory funnel
  4. washwashed with ether (2×150 mL)
  5. additionby adding conc. HCl
  6. extractionextracted with ether (2×400 mL)
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-13c33bd9d2ba465fbec17843da9048db
Source dataset
uspto-grants-2011_05
Patent number
US07947710B2

Reaction notes

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