Ethanol → HCID 18960342, compound

HRID 1707922Notes

Reaction equation

HRID 1707922 reaction equation
[CH2:1]([O:3][CH:4]([O:21][CH2:22][CH3:23])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:7]([O:19][CH3:20])[CH:6]=1)[CH3:2].[CH:24]1[CH:25]=[CH:26][C:27](CCO)=[CH:28][CH:29]=1.S([O-])(O)(=O)=O.[K+].[CH2:39](O)[CH3:40]>C1(C)C=CC=CC=1>[C:40]1([CH2:23][CH2:22][O:21][CH:4]([O:3][CH2:1][CH2:2][C:29]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])=[C:7]([O:19][CH3:20])[CH:6]=2)[CH:39]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 60542-PhenylethanolHCID 516920Potassium bisulfateHCID 18960337HCID 18960337, compound

Product 1

HCID 18960342HCID 18960342, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An amount of 1.1 g (3.36 mmol) of 3-methoxy-4-tert.-butoxycarbonyloxy-benzaldehyde diethylacetal was dissolved in 40 ml of dried toluene. After the addition of 0.82 g (6.71 mmol) of phenylethanol and 16 mg of potassium hydrogen sulfate, the resulting mixture was stirred for 2 hours under reflux. The ethanol formed was then distilled off slowly, while more, toluene was added to the mixture. After complete removal of the ethanol, 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 on an oil pump.

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 ethanol
  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 on an oil pump

Sources & evidence

ORD record
ord-20f9f7fb42344091a7053721bc83cb38
Source dataset
uspto-grants-1994_10
Patent number
US05356752

Reaction notes

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