Water → 4-[(4-Hydroxy-2,5-dimethylphenyl)methyl]benzene-1,3-diol

HRID 1625638Notes

Reaction equation

[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.O.O[CH2:22][C:23]1[C:24](CO)=[C:25]([CH3:31])[C:26]([OH:30])=[CH:27][C:28]=1[CH3:29]>C1(C)C=CC=CC=1.C(O)(=O)C>[OH:2][C:1]1[CH:8]=[CH:7][C:6]([CH2:22][C:23]2[CH:24]=[C:25]([CH3:31])[C:26]([OH:30])=[CH:27][C:28]=2[CH3:29])=[C:4]([OH:5])[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

22.02 g of resorcinol, 1.90 g of p-toluene sulfonic acid, and 44.04 g of water are put in a 100 ml 4-necked flask, and 7.61 g of 4-hydroxymethyl(hydroxymethyl)-2,5-Xylenol is partly added thereto for one hour while maintaining at room temperature of 25° C. The mixture is reacted for 3 hours at the same temperature. Then, 50 g of acetic acid and 50 g of toluene are added to the reaction mass, separating a phase. The obtained organic layer is washed and concentrated. The obtained precipitate is filtered. The filtered product is rinsed with toluene, dried under reduced pressure for 24 hours, and treated through liquid chromatography, obtaining 7.94 g of 1,3-dihydroxy-4-(4-hydroxy-2,5-dimethyl benzyl)benzene having a purity of 99%.

Workup

customThe mixture is reacted for 3 hours at the same temperature
customseparating a phase
washThe obtained organic layer is washed
concentrationconcentrated
filtrationThe obtained precipitate is filtered
washThe filtered product is rinsed with toluene
customdried under reduced pressure for 24 hours
additiontreated through liquid chromatography

Sources & evidence

ORD record: ord-f1aaadce4d9248c8ad9bd6bbb8694c79
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785103B2

Reaction notes

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