Benzaldehyde → HCID 58880521, compound

HRID 2251727Notes

Reaction equation

HRID 2251727 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)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>C1(C)C=CC=CC=1>[C:14]1([CH:13]2[O:1][CH2:2][C:3]3[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[CH:7][C:8]=3[CH2:9][O:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 114692971,2,4-BenzenetrimethanolHCID 71586775Bentonite

Product 1

HCID 58880521HCID 58880521, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4 g of (3,4-bis-hydroxymethylphenyl)methanol (23.8 mmol), 40 ml of toluene, 3.06 g of benzaldehyde (28.5 mmol) and 0.24 g of Montmorillonite KSF (10 mg/mmol) are introduced into a flask equipped with a Dean-Stark. The medium is heated under reflux for 3 hours. After filtration, the toluene is evaporated under vacuum at 30° C. The residue is chromatographed on silica gel (heptane/ethyl acetate=7/3) to give 1.8 g of (7-phenyl)-(5H,9H)-6,8-dioxabenzocyclohepten-2-yl)methanol in the form of a white powder.

Workup

  1. customequipped with a Dean-Stark
  2. temperatureThe medium is heated
  3. temperatureunder reflux for 3 hours
  4. filtrationAfter filtration
  5. customthe toluene is evaporated under vacuum at 30° C
  6. customThe residue is chromatographed on silica gel (heptane/ethyl acetate=7/3)
  7. customto give 1.8 g of (7-phenyl)-(5H,9H)-6,8-dioxabenzocyclohepten-2-yl)methanol in the form of a white powder

Sources & evidence

ORD record
ord-5c457302a00d46b0b62317a6d80cddf4
Source dataset
uspto-grants-2008_01
Patent number
US07319155B2

Reaction notes

Loading…