Ethanol → HCID 22600129, compound

HRID 1760016Notes

Reaction equation

HRID 1760016 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[C:7]([CH3:9])[CH:8]=1.[CH:16](OCC)=[O:17].CCO.O>CCOCC>[O:17]=[CH:16][CH:10]([C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 962WaterHCID 8025Ethyl formateHCID 22600115Ethyl 3-methoxy-5-methylbenzeneacetate

Product 1

HCID 22600129HCID 22600129, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 3-methoxy-5-methylphenylacetate (3.0 g; 14 mmol; is from step (iv) above) and ethyl formate (1.9 g; 26 mmol) in ether (75 mL) was added Na (0.39 g; 17 mmol) in small lumps. The solution was cooled to 0° C. and EtOH (abs.; 0.24 mL) was then added. To the resulting slurry was added ether (100 μL), EtOH (5 mL) and water until the slurry was dissolved. The aqueous phase was collected, acidified to pH 2 (HCl/aq) and extracted with ether. The organic phase was washed with NaHCO3/aq, dried (Na2SO4), and evaporated to yield 2 g (59%) of the sub-title compound.

Workup

  1. dissolutionwas dissolved
  2. customThe aqueous phase was collected
  3. extractionextracted with ether
  4. washThe organic phase was washed with NaHCO3/aq
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-758321f62d2945fa919f1255da1e8fea
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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