Acetic Acid → HCID 53637473, compound

HRID 361986Notes

Reaction equation

HRID 361986 reaction equation
[OH:1][C:2]1[C:27]([CH3:28])=[CH:26][C:5]([CH2:6][C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[CH:10]=[C:9]([CH2:15][C:16]3[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[CH:18][C:17]=3[CH3:24])[C:8]=2[OH:25])=[C:4]([CH3:29])[CH:3]=1.[OH-:30].[Na+].O.[CH2:33]=O.[C:35]([OH:38])(=O)C>O1CCCC1>[OH:1][C:2]1[C:27]([CH3:28])=[CH:26][C:5]([CH2:6][C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[CH:10]=[C:9]([CH2:15][C:16]3[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[C:18]([CH2:33][OH:30])[C:17]=3[CH3:24])[C:8]=2[OH:25])=[C:4]([CH3:29])[C:3]=1[CH2:35][OH:38]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 539253364,4'-[(2-Hydroxy-4,5-dimethyl-1,3-phenylene)bis(methylene)]bis(2,5-dimethylphenol)

Product 1

HCID 53637473HCID 53637473, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Into a 100 ml four-necked flask were charged 5.86 g of above-obtained 2,6-bis(4-hydroxy-2,5-dimethylbenzyl)-3,4-dimethylphenol having a purity of 95.7%, 2.16 g of sodium hydroxide, 21.6 g of water and 2.16 g of tetrahydrofuran and they were completely dissolved. While stirring at 40° C., 7.30 g of 37% formaldehyde was added dropwise thereto over 1 hour, and the reaction was conducted for one more hour. After completionof reaction, 3 g of 90% aqueous acetic acid solution was added for neutralization, and then the mixture was cooled to 25° C. and filtered. The filter cake was dissolved in a mixed solvent consisting of 100 g of ethyl acetate and 100 g of toluene. The resulting solution was washed with water and the oil phase was concentrated. To the concentrated mass, 100 g of toluene was added, and the mixture was cooled to 20°C., and then filtered. The filter cake was rinsed with 100 g of toluene anddried a whole day and night under reduced pressure at 45° C. to obtain 6.76 g of 2,6-bis(4-hydroxy-3-hydroxymethyl-2,5-dimethylbenzyl)-3,4-dimethylphenol.

Workup

  1. dissolutionwere completely dissolved
  2. additionwas added for neutralization
  3. temperaturethe mixture was cooled to 25° C.
  4. filtrationfiltered
  5. dissolutionThe filter cake was dissolved in a mixed solvent
  6. washThe resulting solution was washed with water
  7. concentrationthe oil phase was concentrated
  8. additionTo the concentrated mass, 100 g of toluene was added
  9. temperaturethe mixture was cooled to 20°C.
  10. filtrationfiltered
  11. washThe filter cake was rinsed with 100 g of toluene
  12. waitanddried a whole day and night under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-c05f27c4f5c0408bbde1b91fb7224ab0
Source dataset
uspto-grants-1999_02
Patent number
US05866724

Reaction notes

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