Hydrochloric Acid → 2-(4-formylphenyl)acetic Acid

HRID 1529532Notes

Reaction equation

HRID 1529532 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.C1N2CN3CN(C2)CN1C3.Cl.C(Cl)Cl.C([OH:29])C>O>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=[O:29]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4101HexamethylenetetramineHCID 6344DichloromethaneHCID 45190564-(Bromomethyl)phenylacetic acid

Product 1

HCID 113441872-(4-formylphenyl)acetic AcidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 2-[4-(bromomethyl)phenyl]acetic acid (770 mg, 3.36 mmol) in ethanol (6 mL) and water (6 mL) was added hexamethylenetetramine (1.26 g, 9.0 mmol) and the mixture was heated to reflux for 4 hours. Concentrated HCl (1.5 mL) was added cautiously to the mixture at reflux. The mixture was heated to reflux for 30 minutes and then allowed to cool. Water (20 mL) and DCM (20 mL) were added and the organic phase was passed through a hydrophobic fit and the solvent was removed in vacuo to afford the title compound as an off-white solid (479 mg, 87%). 1H NMR (400 MHz, CDCl3): δ 10.01 (s, 1H), 7.86 (d, J=7.9 Hz, 2H), 7.47 (d, J=7.9 Hz, 2H), 3.75 (s, 2H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureat reflux
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 30 minutes
  6. temperatureto cool
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-484f018c098b449fbfb846ef82fd9d78
Source dataset
uspto-grants-2015_07
Patent number
US09090606B2

Reaction notes

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