Acetic Acid → HCID 21182457, compound

HRID 1386583Notes

Reaction equation

HRID 1386583 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 (4ml), 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-f63c1e35e500466c8d6cb45e8645da6c
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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