Acetic Acid → HCID 21182457, compound

HRID 1872365Notes

Reaction equation

HRID 1872365 reaction equation
C[C:2]([CH3:9])([C:6]([O-:8])=[O:7])[C:3]([O-:5])=[O:4].O[C:11]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:16]=[CH:15][C:12]=1C=O.N1CCCC[CH2:29]1.C(O)(=O)C>CO>[CH2:20]([O:19][C:17]1[CH:16]=[C:15]2[C:12]([CH:9]=[C:2]([C:3]([O:5][CH3:29])=[O:4])[C:6](=[O:7])[O:8]2)=[CH:11][CH:18]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 6946994DimethylmalonatHCID 10060673Benzaldehyde, 2-hydroxy-4-(octyloxy)-

Product 1

HCID 21182457HCID 21182457, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of dimethylmalonate (4 ml), 2-hydroxy-4-octyloxybenzaldehyde (2.50 g) and piperidine (0.1 ml) in methanol (10 ml) was added acetic acid (0.01 ml), and the mixture was stirred for 3 hours at 70° C. The solvents were removed under reduced pressure, and the residue was dissolved in ethyl acetate, and washed with 0.5N hydrochloric acid, water and brine, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and filtrate was evaporated under reduced pressure, and the precipitate was collected by filtration, and washed with n-hexane, and dried to give Methyl 7-octyloxycoumarin-3-carboxylate (0.94 g).

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 0.5N hydrochloric acid, water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. customfiltrate was evaporated under reduced pressure
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with n-hexane
  9. customdried

Sources & evidence

ORD record
ord-595877a5b02a48c1a4a142560df141ca
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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