Hydrochloric Acid → HCID 4715298, compound

HRID 2055925Notes

Reaction equation

HRID 2055925 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1.Br[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C(O)C.O>[CH2:16]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:13][CH:14]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3224-Coumaric acidHCID 7666Phenethyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 4715298HCID 4715298, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Aqueous 1N Sodium hydroxide solution (6.0 mL, 12.0 mmol) was added to a solution of 4-hydroxycinnamic acid (536.0 mg, 3.2 mmol) in ethanol (10.0 mL). 2-Bromoethylbenzene (575.0 mg, 3.1 mmol) was then added to the reaction mixture and the resulting reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure to afford a white residue, which was taken up in water. The aqueous phase was then acidified with concentrated hydrochloric acid to produce a white precipitate which was isolated by filtration and washed with water, then dried to afford (544.0 mg, 66.8%) of the desired 4-phenethyloxycinnamic acid as a white powder. 1H NMR (300 MHz, DMSO) δ 3.82 (3H, s, OCH3), 4.78 (2H, s, CH2), 6.92 (2H, d, 2×ArH, J=7.5 Hz), 7.16 (2H, d, 2×ArH, J=7.5 Hz), 7.52-7.60 (1H, m, ArH), 7.62-7.72 (1H, m, ArH), 7.98 (1H, m, ArH).

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was evaporated under reduced pressure
  3. customto afford a white residue, which
  4. customto produce a white precipitate which
  5. customwas isolated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b076f7733d08411da19a56fc11532595
Source dataset
uspto-grants-2008_02
Patent number
US07332631B2

Reaction notes

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