Toluene → HCID 22360058, compound

HRID 1780011Notes

Reaction equation

HRID 1780011 reaction equation
[C:1]1(C)C=CC=C[CH:2]=1.C(OCC)(=O)C.[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH:25]=[O:26])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH:25]([OH:26])[CH2:1][CH3:2])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 806713-Benzyloxy-4-methoxybenzaldehyde

Product 1

HCID 22360058HCID 22360058, compound

Procedure

To a three-neck flask, 187 ml of a 30M ethyl magnesium bromide ether solution was poured and stirred for 5 minutes under ice cooling. To this solution, 400 ml of a toluene solution in which 123.51 g of 3-benzyloxy-4-methoxybenzaldehyde was dissolved, and the mixture was added dropwise from a dropping funnel over 20 minutes. The reaction solution was stirred for additional 2 hours under ice cooling. After the completion of the reaction, the reaction solution was diluted by adding 300 ml of ethyl acetate. Further, pulverized sodium sulfate decahydrates was added to the reaction solution, which was stirred for 2 hours until a precipitate becomes smoothly. After allowed to stand still for 3 hours, the reaction solution was filtered under reduced pressure, separating into a supernatant and a precipitate. The supernatant was concentrated to dryness, affording 140.57 g of 1-(3'-benzyloxy-4'-methoxyphenyl) propanol.

Workup

  1. additionthe mixture was added dropwise from a dropping funnel over 20 minutes
  2. stirringThe reaction solution was stirred for additional 2 hours under ice cooling
  3. customAfter the completion of the reaction
  4. additionthe reaction solution was diluted
  5. additionwas added to the reaction solution, which
  6. stirringwas stirred for 2 hours until a precipitate
  7. waitto stand still for 3 hours
  8. filtrationthe reaction solution was filtered under reduced pressure
  9. customseparating into a supernatant
  10. concentrationThe supernatant was concentrated to dryness

Sources & evidence

ORD record
ord-c6b1f2c44f2842198f30b6bc1e77a249
Source dataset
uspto-grants-1997_05
Patent number
US05629340

Reaction notes

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