Formaldehyde → 2-(Hydroxymethyl)-4-nonylphenol

HRID 397219Notes

Reaction equation

[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[OH-:17].[Na+].[CH2:19]=O>>[OH:17][CH2:19][C:14]1[CH:15]=[C:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:11]=[CH:12][C:13]=1[OH:16]

Participants

Reactant 3

HCID 712Formaldehyde

HCID 17524-Nonylphenol

HCID 14798Sodium Hydroxide

Product 1

HCID 219511382-(Hydroxymethyl)-4-nonylphenol

Procedure

The general procedure of Example 35 was repeated except that 50 grams of p-nonyl phenol (0.227 mole) was used, along with 9.73 grams (0.238 mole) of 98% sodium hydroxide and 23.0 grams (0.284 mole) of the formaldehyde solution to obtain the intermediate 2-hydroxymethyl-4-nonyl phenol. The desired product, 2-(2-hydroxyethyl)thiomethyl-4-nonyl phenol, was obtained from 23.85 grams (0.095 mole) of the intermediate and 7.4 grams of the 2-mercaptoethanol (0.095 mole) in 50 ml of toluene, along with 0.10 gram of the catalyst. Structural formula 27 for the product was confirmed by 1H and 13C NMR.

Sources & evidence

ORD record: ord-53836bf4368349dcbfa4acd085b9bd37
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610218B1

Reaction notes

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