Hydrochloric Acid → 3-(3,4,5-Trimethoxyphenyl)-2-(4-fluorophenyl)acrylic acid

HRID 444723Notes

Reaction equation

HRID 444723 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[CH:17]=O.CC(OC(C)=O)=O.CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.CO>[CH3:25][O:24][C:20]1[CH:19]=[C:16]([CH:17]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([OH:11])=[O:10])[CH:15]=[C:14]([O:13][CH3:12])[C:21]=1[O:22][CH3:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 68583,4,5-TrimethoxybenzaldehydeHCID 7918Acetic AnhydrideHCID 98372-(4-Fluorophenyl)acetic acidHCID 81531Diisopropylethylamine

Product 1

HCID 684909393-(3,4,5-Trimethoxyphenyl)-2-(4-fluorophenyl)acrylic acidYield 56%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 4-fluoro phenyl acetic acid (2 g, 13 mmol), 3,4,5 trimethoxybenzaldehyde (2.5 g, 13 mmol), Ac2O (10 mL) and DIPEA (2.9 mL, 16.8 mmol) was stirred at room temperature for 12 hours. Upon completion, as monitored by TLC using DCM:MeOH (9:1) as the eluent, 10% aqueous HCl (10 mL) was added to the reaction mixture; the precipitate formed was filtered and dissolved in DCM (100 mL). The organic layer was washed with 10% aqueous NaOH (3×50 mL) and the basic aqueous solution was acidified with 10% aqueous HCl to pH 3. The precipitate formed was filtered, washed with 100 mL water and dried to get the product (2.4 g, 56% yield).

Workup

  1. additionwas added to the reaction mixture
  2. customthe precipitate formed
  3. filtrationwas filtered
  4. dissolutiondissolved in DCM (100 mL)
  5. washThe organic layer was washed with 10% aqueous NaOH (3×50 mL)
  6. customThe precipitate formed
  7. filtrationwas filtered
  8. washwashed with 100 mL water
  9. customdried

Sources & evidence

ORD record
ord-0f84d829b6834248b60c1da22302e30d
Source dataset
uspto-grants-2013_07
Patent number
US08476255B2

Reaction notes

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