3-Hydroxybenzaldehyde → 3-(3-Hydroxyphenyl)-2-propenoic acid

HRID 1611753Notes

Reaction equation

HRID 1611753 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>C(O)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 867Malonic AcidHCID 8082Piperidine

Product 1

HCID 114963-(3-Hydroxyphenyl)-2-propenoic acidYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-hydroxybenzaldehyde (1 g, 0.008 mol), malonic acid (1.69 g, 0.016 mol), piperidine (1 to 3 mL) and acetic acid (10–20 mL) were taken in a 100 ml Erlenmeyer flask and irradiated under microwave for 2–8 minutes in parts. The cooled mixture was poured into ice cold water and extracted with ethyl acetate. The organic layer was washed with dil HCl., saturated sodium chloride and then organic layer dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain crude solid which was recrystallised with methanol, provided a white solid in 76% yield; 193° C. (lit mp 194° C.); 1H NMR (CDCl3) δ 6.73(1H, s, H-3 and H-5), 6.62 (1H, dd, H-7), 5.61(1H, d, J=10.9 Hz trans, H-8), 5.16(1H, d, J=17.6, cis-H-8).; 13C NMR (CDCl3) δ 147.4 (C-2 and C-6), 137.2 (C-1), 135.1 (C-7), 129.5 (C-4), 112.2 (C-8), 103.3 (C-3 and C-5), 56.0 (2 OMe). This experiment clearly indicates that utilization of microwave technique as well as presence of hydroxy at 4-position of phenylaldehydes is important for the preparation of 4-vinylphenols (Example I, II and III).

Workup

  1. customirradiated under microwave for 2–8 minutes in parts
  2. additionThe cooled mixture was poured into ice cold water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with dil HCl
  5. dry with material, saturated sodium chloride and then organic layer dried over sodium sulphate
  6. customThe solvent was evaporated under reduced pressure
  7. customto obtain crude solid which
  8. customwas recrystallised with methanol
  9. customprovided a white solid in 76% yield
  10. custom193° C. (lit mp 194° C.)

Sources & evidence

ORD record
ord-5a352c979eb4442284ed1e6af6681a6e
Source dataset
uspto-grants-2006_01
Patent number
US06989467B2

Reaction notes

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