Formaldehyde → HCID 23499685, compound

HRID 361985Notes

Reaction equation

HRID 361985 reaction equation
[OH:1][C:2]1C=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:27])([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH3:26])[CH:20]=3)[CH3:18])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH3:28].[OH-:29].[Na+].O.[CH2:32]=O.C([O:37][CH2:38][CH3:39])(=O)C>C1(C)C=CC=CC=1.C(O)(=O)C>[OH:1][C:2]1[C:3]([CH3:28])=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([CH3:27])([C:19]3[CH:24]=[C:23]([CH3:32])[C:22]([OH:25])=[C:21]([CH2:26][OH:29])[CH:20]=3)[CH3:18])=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][C:39]=1[CH2:38][OH:37]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 12407526HCID 12407526, compound

Product 1

HCID 23499685HCID 23499685, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Into a 100 ml four-necked flask were charged 29.96 g of 1,4-bis[1-(4-hydroxy-3-methylphenyl)-1-methylethyl]benzene["Bis-OC-P" manufactured by Honshu Kagaku Co., Ltd.], 4.48 g of sodium hydroxide and 44.8 g of water. While stirring at 50° C., 25.97 g of 37% formaldehyde was added dropwise thereto over 1 hour, and the reaction was conducted for 1 more hour. After completion of the reaction, 11 g of 90% aqueous acetic acid solution was added for neutralization and then the mixture was cooled to 25° C. Thereafter, 100 g of ethyl acetate and20 g of toluene were added thereto and a phase separation was carried out. The separated solution was concentrated and 100 g of hexane was added to the concentrated mass and it was cooled to 25° C. The resulting mixture was filtered, and the filtered product was rinsed with 100 g of hexane and dried a whole day and night at 45° C. under reduced pressure to obtain 28.75 g of 1,4-bis[1-(4-hydroxy-3-hydroxymethyl-5-methylphenyl)-1-methylethyl]benzene

Workup

  1. additionwas added for neutralization
  2. temperaturethe mixture was cooled to 25° C
  3. customa phase separation
  4. concentrationThe separated solution was concentrated
  5. addition100 g of hexane was added to the concentrated mass and it
  6. temperaturewas cooled to 25° C
  7. filtrationThe resulting mixture was filtered
  8. washthe filtered product was rinsed with 100 g of hexane
  9. customdried a whole day and night at 45° C. under reduced pressure

Sources & evidence

ORD record
ord-6dbd6a360d6147258a07847131cac87d
Source dataset
uspto-grants-1999_02
Patent number
US05866724

Reaction notes

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