Formaldehyde → 2,6-Dibenzyl-4-(hydroxymethyl)phenol
Reaction equation
[CH:1]([C:24]1[CH:29]=[C:28](CC2C=CC=CC=2)[C:27](O)=[C:26]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:25]=1)([C:3]1[CH:8]=[C:7](CC2C=CC=CC=2)[C:6](O)=[C:5](CC2C=CC=CC=2)[CH:4]=1)C.[CH2:45]=[O:46].[OH-:47].[K+]>C(O)C>[CH2:38]([C:26]1[CH:27]=[C:28]([CH2:45][OH:46])[CH:29]=[C:24]([CH2:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:25]=1[OH:47])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The desired alcohol was prepared by reaction of 2,6-dibenzylphenol with an equivalent of 37% aqueous solution of formaldehyde in ethanol. A solution of 6.85 grams of 2,6-dibenzylphenol in 5 mL ethanol was added to a solution of 1.65 grams 85% KOH in 5 mL ethanol and stirred for 30 minutes. About 1.91 mL of a 37% formalin solution was added dropwise at 25° C. and stirred overnight. The ethanol was removed from the purple solution by rotary evaporation and the residue was dissolved in methylene chloride, washed with saturated ammonium chloride solution and brine, and dried over sodium sulfate. Solvent removal provided 6.6 grams of a crude orange solid which was analyzed by gas chromatography as 4.1 grams starting material 2,6-dibenzylphenol and 2.2 grams 2,6-dibenzyl-4-hydroxymethylphenol (m.p. 116° C.).
Workup
- stirringstirred overnight
- customThe ethanol was removed from the purple solution by rotary evaporation
- dissolutionthe residue was dissolved in methylene chloride
- washwashed with saturated ammonium chloride solution and brine
- dry with materialdried over sodium sulfate
- customSolvent removal
Sources & evidence
- ORD record
- ord-46319aed988a4f1c9010db8af0f8d0f0
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04613642
Reaction notes
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