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

HRID 1611751Notes

Reaction equation

HRID 1611751 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].N1CCCCC1.Cl>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=[CH:16][C:17]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 68583,4,5-TrimethoxybenzaldehydeHCID 8082Piperidine

Product 1

HCID 70213-(3,4,5-Trimethoxyphenyl)acrylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3,4,5-trimethoxybenzaldehyde (5.0 g, 0.025 mol), malonic acid (5.30 g, 0.050 mol), piperidine (4–8 mL) and acetic acid (25–35 mL) were taken in a 100 ml Erlenmeyer flask fitted with a loose funnel at the top. The flask was shaken well and placed inside a microwave oven and irradiated for 4–8 minutes in parts. The cooled mixture was poured into ice cold water and then acidified with 5% HCl. The precipitated yellow solid was filtered and recrystallized with aq. ethanol to afford 3,4,5-trimethoxycinnamic acid in 88% yield; mp 127° C. (lit mp 126–128° C.) whose spectral data was found similar to the reported values 1H NMR (CDCl3) δ 7.73 (1H, d, J=16.0 Hz, —CH═CH—COOH), 6.78 (2H, s, H-2 & H-6), 6.38 (1H, d, J=16.0 Hz, CH═CH—COOH), 3.91 (9H, s, 3-OCH3, 4-OCH3 & 5-OCH3); 13C NMR: δ 172.6 (COOH), 153.8 (C-3 and C-5), 147.4 (C-4), 140.8 (CH═CH—COOH), 129.8 (C-1), 116.8 (CH═CH—COOH), 105.8 (C-2 and C-6), 61.4 (4-OCH3), 56.5 (3-OCH3 and 5-OCH3).

Workup

  1. customfitted with a loose funnel at the top
  2. customplaced inside a microwave oven
  3. customirradiated for 4–8 minutes in parts
  4. additionThe cooled mixture was poured into ice cold water
  5. filtrationThe precipitated yellow solid was filtered
  6. customrecrystallized with aq. ethanol

Sources & evidence

ORD record
ord-e409167595e84ff6a7be4e2d851c332d
Source dataset
uspto-grants-2006_01
Patent number
US06989467B2

Reaction notes

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