Acetic Acid → HCID 53668369, compound

HRID 361976Notes

Reaction equation

HRID 361976 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[C:12]([CH3:13])=[CH:11][C:10]([OH:14])=[C:9]([CH3:15])[CH:8]=2)=[CH:4][C:3]=1[CH3:18].[OH-:19].[Na+].O.[CH2:22]=O.[C:24](O)(=[O:26])C>>[OH:26][CH2:24][C:11]1[C:12]([CH3:13])=[C:7]([CH2:6][C:5]2[CH:16]=[C:17]([CH3:22])[C:2]([OH:1])=[C:3]([CH2:18][OH:19])[CH:4]=2)[CH:8]=[C:9]([CH3:15])[C:10]=1[OH:14]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 544735534-[(4-Hydroxy-3-methylphenyl)methyl]-2,5-dimethylphenol

Product 1

HCID 53668369HCID 53668369, compoundYield 60.8%

Conditions

Temperature
40 °C

Procedure

Into a 100 ml four-necked flask were charged 12.12 g of above-obtained 4-(4-hydroxy-3-methylbenzyl)-2,5-dimethylphenol having a purity of 90.05%,4.8 g of sodium hydroxide and 48 g of water. While stirring at 40° C., 24.35 g of 37% formaldehyde was added dropwise thereto over 1 hour, and the reaction was conducted for 2 more hours. After completion of the reaction, 10 g of 90% aqueous acetic acid solution was added for neutralization and then the mixture was cooled to 25° C. The resulting mixture was filtered and rinsed with 100 g of deionized water. The filtered product was dissolved in 200 g of ethyl acetate, 50 g of toluene was added thereto and the resulting mixture was concentrated. To the concentrated mass, 200 g of toluene was added, and the mixture was cooled to 20° C., and then filtered. The filter cake was rinsed with 200 g of toluene and dried a whole day and night under reduced pressure at 45° C. to obtain 9.20 g of 2-hydroxymethyl-4-(4-hydroxy-3-hydroxymethyl-5-methylbenzyl)-3,6-dimethylphenol.

Workup

  1. additionwas added for neutralization
  2. temperaturethe mixture was cooled to 25° C
  3. filtrationThe resulting mixture was filtered
  4. washrinsed with 100 g of deionized water
  5. dissolutionThe filtered product was dissolved in 200 g of ethyl acetate
  6. addition50 g of toluene was added
  7. concentrationthe resulting mixture was concentrated
  8. additionTo the concentrated mass, 200 g of toluene was added
  9. temperaturethe mixture was cooled to 20° C.
  10. filtrationfiltered
  11. washThe filter cake was rinsed with 200 g of toluene
  12. customdried a whole day and night under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-f81800c7ee0f4f588c9c414ab13f3ab4
Source dataset
uspto-grants-1999_02
Patent number
US05866724

Reaction notes

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