Acetic Acid → HCID 70513115, compound

HRID 1995237Notes

Reaction equation

HRID 1995237 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:15](O)(=[O:17])C.C=O.S(=O)(=O)(O)O>O>[C:1]1([CH2:11][C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:15]=[O:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 68621-Naphthaleneacetic Acid

Product 1

HCID 70513115HCID 70513115, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Into a flask was charged 18.6 g (0.100 mole) 1-naphthylacetic acid, 93 ml. glacial acetic acid, and 8.1 g (0.100 mole) 37% formaldehyde. With stirring, 5.6 ml. (0.100 mole) 96% sulfuric acid was added and the mixture heated at a gentle reflux (110° C.) for about 21 hours. On cooling to room temperature and dilution with 200 ml. water, heavy deposition of solids took place. The polymeric solids were filtered, washed with water, re-slurried in 200 ml. boiling water, and filtered hot. The moist solids were dried in vacuo at 60° C. to give 17.3 g of the 1-naphthylacetic acid/formaldehyde polymer, a tan colored powder.

Workup

  1. temperaturethe mixture heated at
  2. temperatureOn cooling to room temperature
  3. filtrationThe polymeric solids were filtered
  4. washwashed with water, re-slurried in 200 ml
  5. filtrationboiling water, and filtered hot
  6. customThe moist solids were dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-82f46c05df33405285ff8987603f174b
Source dataset
uspto-grants-1983_09
Patent number
US04403089

Reaction notes

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