Potassium Carbonate → HCID 20600101, compound

HRID 1739496Notes

Reaction equation

HRID 1739496 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=1[O:14][CH3:15].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:15][O:14][C:3]1[CH:4]=[C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:11])=[O:9])[CH:12]=[CH:13][C:2]=1[O:1][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 779706-Bromo-1-hexanolHCID 5357283Methyl Ferulate

Product 1

HCID 20600101HCID 20600101, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 0.5 g of methyl (E)-4-hydroxy-3-methoxycinnamate, 10 ml of 2-butanone, 0.35 ml of 6-bromohexanol and 1 g of ground potassium carbonate was heated under reflux for 5 hrs. Then, the reaction mixture was cooled and partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulphate, filtered and evaporated. Chromatography on 100 g of silica gel with toluene/ethyl acetate (1:1) gave 750 ml of methyl (E)-3-[3-methoxy-4-(6-hydroxyhexyloxy)phenyl]acrylate as a colorless solid, λmax. (CH2Cl2): 323 nm (ε=20513).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hrs
  3. temperatureThen, the reaction mixture was cooled
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-48d1593fd5964939b90cf59925df9c04
Source dataset
uspto-grants-1999_10
Patent number
US05965761

Reaction notes

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