1,2,4-Benzenetrimethanol → HCID 58880522, compound

HRID 2251726Notes

Reaction equation

HRID 2251726 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[CH:7][C:8]=1[CH2:9][OH:10].[CH:13]([O-])([O-])[O:14][CH3:15].O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>COCCOC>[CH3:13][O:14][CH:15]1[O:1][CH2:2][C:3]2[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[CH:7][C:8]=2[CH2:9][O:10]1

Participants

5

Reactant 3

HCID 114692971,2,4-BenzenetrimethanolHCID 53629101MethylorthoformateHCID 71586775Bentonite

Product 1

HCID 58880522HCID 58880522, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

4 g of (3,4-bis-hydroxymethylphenyl)methanol (23.8 mmol), 40 ml of 1,2-dimethoxyethane, 2.78 g of methyl orthoformate (26.2 mmol) and 0.24 g of Montmorillonite KSF (10 mg/mmol) are introduced into a flask. The reaction medium is stirred at room temperature for 4 hours 30 minutes and then the montmorillonite is filtered off and the 1,2-dimethoxyethane is evaporated under vacuum at 30° C. The residue is chromatographed on silica gel (dichloromethane/methanol=98/2) to give 3.2 g of (7-methoxy)-(5H,9H)-6,8-dioxabenzocyclohepten-2-yl)methanol in the form of an oil.

Workup

  1. filtrationthe montmorillonite is filtered off
  2. customthe 1,2-dimethoxyethane is evaporated under vacuum at 30° C
  3. customThe residue is chromatographed on silica gel (dichloromethane/methanol=98/2)
  4. customto give 3.2 g of (7-methoxy)-(5H,9H)-6,8-dioxabenzocyclohepten-2-yl)methanol in the form of an oil

Sources & evidence

ORD record
ord-bc61d4c8ba014a8ab113c97ce54e4b14
Source dataset
uspto-grants-2008_01
Patent number
US07319155B2

Reaction notes

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