1-Bromohexane → HCID 20230834, compound

HRID 2298727Notes

Reaction equation

HRID 2298727 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][CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:15]([O:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 5319562Methyl-P-Coumarate

Product 1

HCID 20230834HCID 20230834, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Trans methyl 4-hydroxycinnamate (20.0 g, 11.2 mmol), 1-bromohexane (18.5 g, 112 mmol) and potassium carbonate (16.6 g, 120 mmol) were stirred under reflux in butanone. The mixture was allowed to cool after 16 hours, evaporated to dryness and the residue was partitioned between DCM and water. The DCM layer was removed and dried (Na2SO4) and evaporated to leave a yellow solid methyl (E)-3-(4-hexyloxyphenyl)-2-propenoate which was recrystallized from petroleum. Yield=20.0 g, 71%.

Workup

  1. temperatureto cool after 16 hours
  2. customevaporated to dryness
  3. customthe residue was partitioned between DCM and water
  4. customThe DCM layer was removed
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-064d0e21d4c546e99af7e21b7da70c97
Source dataset
uspto-grants-2002_12
Patent number
US06495217B2

Reaction notes

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