Hydrochloric Acid → HCID 20062264, compound

HRID 703371Notes

Reaction equation

HRID 703371 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6]CC)=O.[OH:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22](=[O:24])[CH3:23])[CH:17]=[CH:18][CH:19]=1.Cl>C(O)C.O.C(Cl)Cl>[OH:6][C:4]1[CH:3]([C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([OH:13])[CH:15]=2)[CH2:21][C:22](=[O:24])[CH:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 5360545SodiumHCID 53426253HCID 53426253, compound

Product 1

HCID 20062264HCID 20062264, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent3×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.72 g (0.205 mol) of freshly cut sodium metal dissolved in absolute ethanol was added 16.8 g (0.105 mol) of diethyl malonate in 25 mL of absolute ethanol. To this solution was added 16.2 g (0.10 mol) of 1-(3-hydroxyphenyl)but-1-en-3-one, prepared as described by Marrion et al. in J. Biochem. vol. 45, 533, (1949), and 100 mL of absolute ethanol. The solution was stirred at ambient temperature for 17 hours, diluted with 500 mL of water and acidified with 19 mL of concentrated HCl. The mixture was diluted with 400 mL of methylene chloride and the organic layer separated, washed with 150 mL of water and dried over Na2SO4. The solvent was removed in vacuo leaving 26.5 g (96 percent of theoretical) of the above named product as a light yellow oil; 1H NMR (CDCl3 +D6 --DMSO) δ 0.8- 1.3 (m, 3H, --CH2CH3), 2.3-4.3 (m, 6H, ring protons and --CH2CH3), 5.5 (s, 1H, --CH=), 6.5-7.2 (m, 4H, ArH), 6.8 (b, 1H, ArOH), 18.0 (b, 1H, OH).

Workup

  1. customprepared
  2. customthe organic layer separated
  3. washwashed with 150 mL of water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customleaving 26.5 g (96 percent of theoretical) of the above named product as a light yellow oil

Sources & evidence

ORD record
ord-043b546df5a9400d9e8c150c2243d37c
Source dataset
uspto-grants-1991_01
Patent number
US04983211

Reaction notes

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