Hydrochloric Acid → HCID 178418889, compound

HRID 1374878Notes

Reaction equation

HRID 1374878 reaction equation
CO[C:3](=[O:8])[C:4]([O:6][CH3:7])=[O:5].C[O-].[Na+].[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1.Cl>C1(C)C=CC=CC=1.C(Cl)Cl.CCCCCC.CCOC(C)=O>[OH:8]/[C:3](=[CH:21]\[C:20]([C:17]1[CH:18]=[CH:19][C:14]([S:13][CH3:12])=[CH:15][CH:16]=1)=[O:22])/[C:4]([O:6][CH3:7])=[O:5]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11120Dimethyl oxalateHCID 745011-(4-(Methylthio)phenyl)ethan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 178418889HCID 178418889, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Dimethyloxalate (26 g, 180.7 mmol) was added to a stirred suspension of sodium methoxide (9.75 g, 180.7 mmol) in dry toluene (200 mL) at 0° C. The white suspension was stirred for 15 min at 0° C. A solution of 4′-(methylthio)acetophenone (15 g, 90.4 mmol) in dry toluene (150 mL) was then added dropwise over 15 min giving a yellow suspension which was stirred for 2 hours at room temperature. The thick yellow suspension was transferred to a 2 liter flask and stirred vigorously with 10% HCl (250 mL) and EtOAc (200 mL) to dissolve all the solids present. The organic layer was separated and the aqueous layer was extracted with EtOAc (100 mL). The combined organic extracts were washed with water (250 mL), dried over Na2SO4 and the solvent was evaporated under reduced pressure to give thick brown oil. The brown oil was dissolved in CH2Cl2 (25 mL) and hexane (125 mL) and left in a freezer at −20° C. for 16 hours to give the title compound (18 g, 79%) as orange color solid. mp 81° C. 1H-NMR (300 MHz, CDCl3) δ 7.83 (d, J=8.6 Hz, 2H), 7.23 (d, J=8.6 Hz, 2H), 6.97 (s, 1H), 3.89 (s, 3H), 2.47 (s, 3H); 13C-NMR (75 MHz, CDCl3); mass spectrum (API-TIS) m/z 253 (MH+)

Workup

  1. customgiving a yellow suspension which
  2. stirringwas stirred for 2 hours at room temperature
  3. customThe thick yellow suspension was transferred to a 2 liter flask
  4. dissolutionto dissolve all the solids present
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with EtOAc (100 mL)
  7. washThe combined organic extracts were washed with water (250 mL)
  8. dry with materialdried over Na2SO4
  9. customthe solvent was evaporated under reduced pressure
  10. customto give thick brown oil

Sources & evidence

ORD record
ord-a9147339636d4057ae7a169256e8d515
Source dataset
uspto-grants-2007_01
Patent number
US07166618B2

Reaction notes

Loading…