Formaldehyde → HCID 54499868, compound

HRID 361980

Reaction equation

HRID 361980 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH3:21])[CH:15]=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[CH3:22].[OH-:23].[Na+].[OH2:25].[CH2:26]=[O:27].[C:28]1(C)C=CC=CC=1>C(OCC)(=O)C.C(O)(=O)C>[OH:23][C:21]1[C:18]([CH3:28])=[CH:19][C:14]([C:8]2([C:5]3[CH:4]=[C:3]([CH3:22])[C:2]([OH:25])=[C:7]([CH2:26][OH:27])[CH:6]=3)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[CH:15][C:16]=1[CH2:17][OH:20]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 962WaterHCID 1140TolueneHCID 14798Sodium HydroxideHCID 75386Phenol, 4,4'-cyclohexylidenebis[2-methyl-

Product 1

HCID 54499868HCID 54499868, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Into a 100 ml four-necked flask were charged 23.71 g of 1,1-bis(4-hydroxy-3-methylphenyl)-cyclohexane["Bis-OC--Z" 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 28.5 g of 1,1-bis(4-hydroxy-3-hydroxymethyl-5-methylphenyl)-cyclohexane.

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-e22b4faf3fa448dfbf51445fe93527a2
Source dataset
uspto-grants-1999_02
Patent number
US05866724

Linked notes

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