Formaldehyde → HCID 54076525, compound

HRID 361981Notes

Reaction equation

HRID 361981 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH:18]([CH3:20])[CH3:19])[CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH:21]([CH3:23])[CH3:22].[OH-:24].[Na+].O.[CH2:27]=O.[C:29](OCC)(=[O:31])C>C1(C)C=CC=CC=1.C(O)(=O)C>[OH:1][C:2]1[C:3]([CH:21]([CH3:23])[CH3:22])=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[C:13]([CH:18]([CH3:19])[CH3:20])[C:14]([OH:17])=[C:15]([CH2:29][OH:31])[CH:16]=2)([CH3:10])[CH3:9])=[CH:6][C:7]=1[CH2:27][OH:24]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2285372,2-Bis(4-hydroxy-3-isopropylphenyl)propane

Product 1

HCID 54076525HCID 54076525, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Into a 100 ml four-necked flask were charged 25.00 g of 2,2-bis(4-hydroxy-3-isopropylphenyl)propane["Bis-OIPP-A" 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 and 20 g of toluene were added thereto and a phase separation was carried out. Then, the resulting mixture was concentrated to obtain 28.2 g of 2,2-bis(4-hydroxy-3-hydroxymethyl-5-isopropylphenyl)propane.

Workup

  1. additionwas added for neutralization
  2. temperaturethe mixture was cooled to 25° C
  3. customa phase separation
  4. concentrationThen, the resulting mixture was concentrated

Sources & evidence

ORD record
ord-6bd1b33dc05f406d8b0d120bac2af302
Source dataset
uspto-grants-1999_02
Patent number
US05866724

Reaction notes

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