Methanol → HCID 18960339, compound

HRID 1707919Notes

Reaction equation

HRID 1707919 reaction equation
[CH3:1][O:2][CH:3]([O:18][CH3:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][CH:5]=1.[O:20]([CH2:27]CO)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S([O-])(O)(=O)=O.[K+].[CH3:36][OH:37].[C:38]1(C)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[O:37]([CH2:36][CH2:19][O:18][CH:3]([O:2][CH2:1][CH2:27][O:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[CH:8][CH:9]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 1140TolueneHCID 31236PhenoxyethanolHCID 516920Potassium bisulfateHCID 18960338HCID 18960338, compound

Product 1

HCID 18960339HCID 18960339, compound

Procedure

A mixture of 2 g (7.45 mmol) of 4-(tert.-butoxycarbonyloxy)-benzaldehyde dimethylacetal, 2.06 g (14.9 mmol) of 2-phenoxyethanol and 40 mg of potassium hydrogensulfate was heated to the boil in 30 ml of dried toluene under a reflux condenser. After heating for 1 hour, the methanol formed was distilled off slowly, while more toluene was added to the mixture. After complete removal of the methanol, the mixture was cooled down, the potassium hydrogen sulfate catalyst was filtered off and the toluene was stripped off. The oily residue was dissolved in dichloromethane and washed with water. The organic phase was dried over magnesium sulfate. After the solvent had been stripped off under reduced pressure, the product was dried in an oil pump vacuum.

Workup

  1. temperatureAfter heating for 1 hour
  2. distillationwas distilled off slowly
  3. additionwhile more toluene was added to the mixture
  4. customAfter complete removal of the methanol
  5. temperaturethe mixture was cooled down
  6. filtrationthe potassium hydrogen sulfate catalyst was filtered off
  7. dissolutionThe oily residue was dissolved in dichloromethane
  8. washwashed with water
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. customthe product was dried in an oil pump vacuum

Sources & evidence

ORD record
ord-9ff583a7b94347ae89c9dbccde130a47
Source dataset
uspto-grants-1994_10
Patent number
US05356752

Reaction notes

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