Sodium Hydroxide → HCID 14514984, compound

HRID 1003976Notes

Reaction equation

HRID 1003976 reaction equation
[O:1]([CH2:8][CH2:9][CH:10]([C:16]([O:18]CC)=[O:17])[C:11]([O:13]CC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[O:1]([CH2:8][CH2:9][CH:10]([C:16]([OH:18])=[O:17])[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 458161HCID 458161, compound

Product 1

HCID 14514984HCID 14514984, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Diethyl 2-phenoxyethylmalonate (1 g) was treated with sodium hydroxide (285 mg, 2 eq) in ethanol (10 ml) and water (5 ml). After 16 h the solution was diluted with water (10 ml), washed with diethyl ether (3×20 ml), acidified to pH 2 (5M hydrochloric acid) and extracted with ethyl acetate (2×20 ml). The combined extracts were washed with water (3×20 ml), saturated brine (20 ml), dried (MgSO4) and evaporated to yield the title compound (510 mg, 64%). νmax (KBr) 2915 (br), 1730 and 1243 cm-1. δH [(CD3)2CO] 2.36 (2H, m, CH2CH), 3.69 (1H, t, J 7.2 Hz, CH), 4.12 (2H, t, J 7.3 Hz, OCH2), 6.94, 7.28 (5H, m, Ph). EIMS M+ 224, DCIMS MNH4+ 242.

Workup

  1. washwashed with diethyl ether (3×20 ml)
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. washThe combined extracts were washed with water (3×20 ml), saturated brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-3f090cc974aa46f5bfb0a2ef9434d759
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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