Acetic Acid → HCID 54251996, compound

HRID 361984Notes

Reaction equation

HRID 361984 reaction equation
[OH:1][C:2]1[C:28]([CH3:29])=[CH:27][C:5]([CH2:6][C:7]2[C:12]([CH3:13])=[C:11]([CH2:14][C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[CH:17][C:16]=3[CH3:23])[C:10]([CH3:24])=[C:9]([CH3:25])[C:8]=2[OH:26])=[C:4]([CH3:30])[CH:3]=1.[OH-:31].[Na+].O.[CH2:34]=O.[C:36]([OH:39])(=O)C>>[OH:1][C:2]1[C:28]([CH3:29])=[CH:27][C:5]([CH2:6][C:7]2[C:12]([CH3:13])=[C:11]([CH2:14][C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH2:34][OH:31])[C:16]=3[CH3:23])[C:10]([CH3:24])=[C:9]([CH3:25])[C:8]=2[OH:26])=[C:4]([CH3:30])[C:3]=1[CH2:36][OH:39]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 544729154,4'-[(4-Hydroxy-2,5,6-trimethyl-1,3-phenylene)bis(methylene)]bis(2,5-dimethylphenol)

Product 1

HCID 54251996HCID 54251996, compoundYield 79.2%

Conditions

Temperature
40 °C

Procedure

Into a 500 ml four-necked flask were charged 40.45 g of above-obtained 2,4-bis(4-hydroxy-2,5-dimethylbenzyl)-3,5,6-trimethylphenol having a purity of 99.38%, 14.4 g of sodium hydroxide, 144 g of water and 14.4 g oftetrahydrofuran and they were completely dissolved. While stirring at 40° C., 48.69 g of 37% formaldehyde was added dropwise thereto over1 hour, and the reaction was conducted for 3 more hours. After completion of the reaction, 18.02 g of 90% aqueous acetic acid solution was added forneutralization and then the mixture was cooled to 25° C. The resulting mixture was filtered and the filtered product was dissolved in amixed solvent consisting of 100 g of ethyl acetate and 14.40 g of tetrahydrofurane. The resulting solution was washed with water and the oilphase was concentrated. To the concentrated product, 100 g of toluene was added, and the mixture was cooled to 20° C., and then filtered. Thefilter cake was rinsed with 100 g of toluene and dried a whole day and night under reduced pressure at 45° C. to obtain 36.8 g of 2,4-bis(4-hydroxy-3-hydroxymethyl-2,5-dimethylbenzyl)-3,5,6-trimethylphenol.

Workup

  1. dissolutionwere completely dissolved
  2. additionwas added forneutralization
  3. temperaturethe mixture was cooled to 25° C
  4. filtrationThe resulting mixture was filtered
  5. dissolutionthe filtered product was dissolved in amixed solvent
  6. washThe resulting solution was washed with water
  7. concentrationthe oilphase was concentrated
  8. additionTo the concentrated product, 100 g of toluene was added
  9. temperaturethe mixture was cooled to 20° C.
  10. filtrationfiltered
  11. washThefilter cake was rinsed with 100 g of toluene
  12. customdried a whole day and night under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-e37ccc643cc848de843689c7388de68e
Source dataset
uspto-grants-1999_02
Patent number
US05866724

Reaction notes

Loading…