Methanol → HCID 18960341, compound

HRID 1707921Notes

Reaction equation

HRID 1707921 reaction equation
[CH3:1][O:2][CH:3]([O:18][CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:5]=1.[C:20]1([CH2:26]CO)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.S([O-])(O)(=O)=O.[K+].CO>C1(C)C=CC=CC=1>[C:4]1([CH2:3][CH2:19][O:18][CH:3]([O:2][CH2:1][CH2:26][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH:5]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 60542-PhenylethanolHCID 516920Potassium bisulfateHCID 18960344HCID 18960344, compound

Product 1

HCID 18960341HCID 18960341, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

One g (3.73 mmol) of 3-tert.-butoxycarbonyloxy-benzaldehyde dimethylacetal was dissolved in 40 ml of dried toluene. After addition of 0.91 g (7.46 mmol) of 2-phenylethanol and 18 mg of potassium hydrogen sulfate, the resulting mixture was stirred for 2 hours under reflux. The methanol formed was then distilled off slowly, while more toluene was added to the mixture. After complete removal of the methanol, the mixture was cooled down and the potassium hydrogen sulfate was filtered off. The filtrate was concentrated in a rotary evaporator. This gave a yellowish, viscous oil, which was dried in an oil pump vacuum.

Workup

  1. temperatureunder reflux
  2. distillationwas then 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 was filtered off
  7. concentrationThe filtrate was concentrated in a rotary evaporator
  8. customThis gave a yellowish, viscous oil, which
  9. customwas dried in an oil pump vacuum

Sources & evidence

ORD record
ord-c9a8b67713064eb1899e2842aa1e6500
Source dataset
uspto-grants-1994_10
Patent number
US05356752

Reaction notes

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