Hydroxyphenylacetic acid → 2-(4-Acetoxyphenyl)-3-p-tolylacrylic acid

HRID 2238254Notes

Reaction equation

HRID 2238254 reaction equation
[OH: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][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[C:28](OC(=O)C)(=[O:30])[CH3:29]>O.C(OCC)(=O)C>[C:28]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[CH:12][C:13]2[CH:20]=[CH:19][C:16]([CH3:17])=[CH:15][CH:14]=2)[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)(=[O:30])[CH3:29]

Participants

8

Reactant 5

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 77254-MethylbenzaldehydeHCID 7918Acetic AnhydrideHCID 11430Potassium Carbonate

Product 1

HCID 687943372-(4-Acetoxyphenyl)-3-p-tolylacrylic acidYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of (4-hydroxyphenyl)-acetic acid (18.3 g, 120.3 mmol) and 4-methylbenzaldehyde (12.0 g, 100 mmol) in 250 mL acetic anhydride was added potassium carbonate (11.9 g, 121.2 mmol). The reaction mixture was stirred at 80° C. for 16 h before it was cooled to room temperature. To the mixture was added 100 mL H2O, 5% HCl in water to pH 1 and 200 mL ethyl acetate. The mixture was then heated to 80° C. until all ethyl acetate was evaporated. The precipitate was filtered and washed with water and hexane. The filter cake was recrystallized out of toluene, filtered, washed with hexane and dried under vacuum to yield a pale yellow powder (20.16 g, 68.1%). 1H NMR (400 MHz, DMSO-d6) δ 12.62 (br s, 1H), 7.74 (s, 1H), 7.19 (d, J=8.8 Hz, 2H), 7.13 (d, J=8.8 Hz, 2H), 7.01 (d, J=8.0 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 2.29 (s, 3H), 2.23 (s, 3H).

Workup

  1. temperaturewas cooled to room temperature
  2. customwas evaporated
  3. filtrationThe precipitate was filtered
  4. washwashed with water and hexane
  5. customThe filter cake was recrystallized out of toluene
  6. filtrationfiltered
  7. washwashed with hexane
  8. customdried under vacuum

Sources & evidence

ORD record
ord-ceb663f9160b4a3c9d6073032109b6e1
Source dataset
uspto-grants-2010_05
Patent number
US07718682B2

Reaction notes

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