Formaldehyde → HCID 86738659, compound

HRID 1995236Notes

Reaction equation

HRID 1995236 reaction equation
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:14]=[O:15].S(=O)(=O)(O)O>C(O)(=O)C>[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:14]=[O:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 68471-Naphthoic acid

Product 1

HCID 86738659HCID 86738659, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 17.2 g (0.100 mole) 1-naphthoic acid and 8.1 g (0.100 mole) 37% formaldehyde in 85 ml. glacial acetic acid was stirred and maintained at a temperature of 90°-110° C. during addition of 5.6 ml. (0.100 mole) 96% sulfuric acid over 10 minutes. The solution was maintained at 110° C. for another 24 hours, during which time the solution became progressively darker in color and some solids appeared. On cooling to 50° C., heavy precipitation of white solids occurred. Addition of 150 ml. water produced a heavier deposition of solids which was filtered, washed with water, and dried. The solids were slurried in boiling toluene, filtered hot, and dried to afford 11.1 g of the 1-naphthoic acid/formaldehyde polymer showing a softening point of about 220° C.

Workup

  1. temperaturemaintained at a temperature of 90°-110° C. during addition of 5.6 ml
  2. temperatureOn cooling to 50° C.
  3. customheavy precipitation of white solids
  4. additionAddition of 150 ml
  5. customwater produced a heavier deposition of solids which
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried
  9. filtrationfiltered hot
  10. customdried

Sources & evidence

ORD record
ord-b5ee67de5c1347bdafb0f30d581e6046
Source dataset
uspto-grants-1983_09
Patent number
US04403089

Reaction notes

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