Formaldehyde → HCID 53863828, compound

HRID 361978Notes

Reaction equation

HRID 361978 reaction equation
O[C:2]1[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:3]=1[CH2:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[C:7]([CH3:13])[CH:6]=1.[OH-:20].[Na+].[OH2:22].[CH2:23]=[O:24].[C:25]1(C)C=CC=CC=1>C(OCC)(=O)C.C(O)(=O)C>[OH:20][CH2:25][C:9]1[C:10]([CH3:11])=[C:5]([CH2:4][C:3]2[CH:14]=[C:15]([CH3:19])[C:16]([CH3:18])=[C:17]([CH2:2][OH:22])[C:23]=2[OH:24])[CH:6]=[C:7]([CH3:13])[C:8]=1[OH:12]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 962WaterHCID 1140TolueneHCID 14798Sodium HydroxideHCID 540565984-(2-Hydroxy-4,5-dimethylbenzyl)-2,5-dimethylphenol

Product 1

HCID 53863828HCID 53863828, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Into a 100 ml four-necked flask were charged 7.69 g of the above-obtained 4-(2-hydroxy-4,5-dimethylbenzyl)-2,5-dimethylphenol having purity of 90.85%, 2.88 g of sodium hydroxide and 28.8 g of water and they were dissolved. While keeping the temperature at 40° C., 14.61 g of 37% formaldehyde was added dropwise thereto over one hour, and the mixture wasstirred for one more hour. After completion of the reaction, 6 g of 90% aqueous acetic acid solution was added for neutralization and the mixture was cooled to 25 ° C. Thereafter, 100 g of ethyl acetate and 20 g of toluene were added thereto, followed by a phase separation. The solution thus obtained was concentrated to obtain 9.20 g of 2-hydroxymethyl-4-(2-hydroxy-3-hydroxymethyl-4,5-dimethylbenzyl)-3,6-dimethylphenol

Workup

  1. dissolutionwere dissolved
  2. customat 40° C.
  3. additionwas added for neutralization
  4. customfollowed by a phase separation
  5. customThe solution thus obtained
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-19d181e32a3c4d90991dbe17b35532fa
Source dataset
uspto-grants-1999_02
Patent number
US05866724

Reaction notes

Loading…