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

HRID 1625638
Notes
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Reaction equation

HRID 1625638 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 5054ResorcinolHCID 6101p-Toluenesulfonic acidHCID 86688865HCID 86688865, compound

Product 1

HCID 225083514-[(4-Hydroxy-2,5-dimethylphenyl)methyl]benzene-1,3-diolYield 77.8%

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Solvent
HCID 1140TolueneSolvent

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

  1. customThe mixture is reacted for 3 hours at the same temperature
  2. customseparating a phase
  3. washThe obtained organic layer is washed
  4. concentrationconcentrated
  5. filtrationThe obtained precipitate is filtered
  6. washThe filtered product is rinsed with toluene
  7. customdried under reduced pressure for 24 hours
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes