Ethyl orthoformate → HCID 18972492, compound

HRID 2395094Notes

Reaction equation

HRID 2395094 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH3:22])([CH3:21])[C:8]3[C:13]([O:14][C:15]=2[C:16]=1C=O)=[CH:12][C:11]([O:19][CH3:20])=[CH:10][CH:9]=3.[CH:23]([O:30][CH2:31]C)([O:27][CH2:28]C)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:31][O:30][CH:23]([O:27][CH3:28])[C:12]1[C:13]2[O:14][C:15]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:16]=3)[C:7]([CH3:21])([CH3:22])[C:8]=2[CH:9]=[CH:10][C:11]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 18972613HCID 18972613, compound

Product 1

HCID 18972492HCID 18972492, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 24.15 g of 3,6-dimethoxy-9,9-dimethylxanthene-4-carboxaldehyde in 50 ml of absolute ethanol was treated with 50 ml of triethyl orthoformate. After the addition of 100 mg of p-toluenesulphonic acid monohydrate the mixture was boiled under reflux for 1 hour, then cooled and poured into ice-cold sodium bicarbonate solution, whereupon the mixture was extracted twice with 200 ml of ether each time. The combined extracts were washed neutral with water, dried over Na2SO4 and concentrated. The residue was purified on silica gel with hexane/ethyl acetate, whereby there were obtained 19.6 g of 3,6-dimethoxy-9,9-dimethylxanthene-4-carboxaldehyde dimethyl acetal as a pale yellow oil which crystallized slowly; m.p. 60°-62°, IR 2972, 1606, 1572, 1490 cm-1.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturecooled
  3. additionpoured into ice-cold sodium bicarbonate solution, whereupon the mixture
  4. extractionwas extracted twice with 200 ml of ether each time
  5. washThe combined extracts were washed neutral with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-64fccd2e72e24b86b76dadefc3aef429
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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