Acetic Acid → HCID 11729806, compound

HRID 361982Notes

Reaction equation

[OH:1][C:2]1[C:26]([CH3:27])=[CH:25][C:5]([CH2:6][C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH2:14][C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[CH:17][C:16]=3[CH3:23])[C:8]=2[OH:24])=[C:4]([CH3:28])[CH:3]=1.[OH-:29].[Na+].O.[CH2:32]=O.[C:34]([OH:37])(=O)C>O1CCCC1>[OH:1][C:2]1[C:26]([CH3:27])=[CH:25][C:5]([CH2:6][C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH2:14][C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH2:32][OH:29])[C:16]=3[CH3:23])[C:8]=2[OH:24])=[C:4]([CH3:28])[C:3]=1[CH2:34][OH:37]

Participants

Conditions

Temperature: 40 °C

Procedure

Into a 3 liter four-necked flask were charged 263.6 g of 2,6-bis(4-hydroxy-2,5-dimethylbenzyl)-4-methylphenol, 67.2 g of sodium hydroxide, 1169.3 g of water and 107.5 g of tetrahydrofuran and they were completely dissolved. While stirring at 40° C., 340.9 g of 37% formaldehyde was added dropwise thereto over 1 hour, and the reaction was conducted for 2 more hours. After completion of the reaction, 134.4 g of 90% aqueous acetic acid solution was added for neutralization and then themixture was cooled to 25° C. Thereafter, the precipitated crystalline product was filtered out and rinsed with 1000 g of deionized water. The resulting product was dried a whole day and night under reducedpressure at 45° C. to obtain 265 g of 2,6-bis(4-hydroxy-3-hydroxymethyl-2,5-dimethylbenzyl)-4-methylphenol

Workup

dissolutionwere completely dissolved
additionwas added for neutralization
temperaturethemixture was cooled to 25° C
filtrationThereafter, the precipitated crystalline product was filtered out
washrinsed with 1000 g of deionized water
customThe resulting product was dried a whole day and night under reducedpressure at 45° C.

Sources & evidence

ORD record: ord-37f41450424248a5b912a26a7096f5b5
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866724

Reaction notes

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