Methanol → HCID 18960340, compound

HRID 1707924Notes

Reaction equation

HRID 1707924 reaction equation
[CH3:1][O:2][CH:3]([O:26][CH3:27])[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])[C:5]=1[O:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[C:28]1([CH2:34]CO)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.S([O-])(O)(=O)=O.[K+].CO>C1(C)C=CC=CC=1>[C:4]1([CH2:3][CH2:27][O:26][CH:3]([O:2][CH2:1][CH2:34][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:5]=2[O:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 60542-PhenylethanolHCID 516920Potassium bisulfateHCID 18960336HCID 18960336, compound

Product 1

HCID 18960340HCID 18960340, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An amount of 1.43 g (3.73 mmol) of 2,3-bis-tert.-butoxycarbonyloxy-benzaldehyde dimethylacetal was dissolved in 40 ml of dried toluene. After the addition of 0.91 g (7.46 mmol) of 2-phenylethanol and 18 mg of potassium hydrogen sulfate, the resulting mixture was stirred for 1 hour 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 hydrogensulfate 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 hydrogensulfate 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-4611ce9c5505457eae591c168f16db5a
Source dataset
uspto-grants-1994_10
Patent number
US05356752

Reaction notes

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