Hydrochloric Acid → HCID 69800908, compound

HRID 984422Notes

Reaction equation

HRID 984422 reaction equation
[OH:1][CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Br)=[CH:18][CH:17]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.O>[CH3:12][O:13][C:14](=[O:15])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5](/[CH:4]=[CH:3]/[CH2:2][OH:1])[CH:6]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 12641156HCID 12641156, compound

Product 1

HCID 69800908HCID 69800908, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of (E)-3-(3-Hydroxy-propenyl)-phenol (0.5 g, 3.33 mmol), methyl 4-(bromomethyl) benzoate (763 mg, 3.33 mmol) and potassium carbonate (1.8 g, 13.3 mmol) in acetone (40 ml) was stirred at room temperature over night. The reaction mixtyre was added water (30 ml) and acidified with 1N HCl and extracted with ethyl acetate (90 ml). The organic phase was washed with water, brine and dried with sodium sulphate and evaporated and dried in vacuo yielding 954 mg (96%) (E)-4-[3-(3-Hydroxy-propenyl)-phenoxymethyl]-benzoic acid methyl ester.

Workup

  1. extractionextracted with ethyl acetate (90 ml)
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried with sodium sulphate
  4. customevaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c68ccabd48b94c7db43eb4d9468be20d
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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