Benzaldehyde → HCID 875648, compound

HRID 1953399Notes

Reaction equation

HRID 1953399 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1CCCC1.C1(=O)C2C(=CC=CC=2)CCC1>CO>[CH:14](=[C:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]1=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 107241-TetraloneHCID 141126-Methoxy-alpha-tetraloneHCID 31268Pyrrolidine

Product 1

HCID 875648HCID 875648, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 6-methoxy-1-tetralone (227 mmole, 40 gm) and benzaldehyde (272 mmole, 27.5 mL) in 450 mL of methanol was added pyrrolidine (272 mmole, 23.6 mL). The mixture was stirred at room temperature for about 4 days until TLC indicated that no starting tetralone was present. The mixture was concentrated in vacuo, then dissolved in EtOAc, washed with four portions of 10% HCl, two portions of saturated NaHCO3 solution, and one portion of brine. The solvent was removed in vacuo and the crude oil was triturated with diethyl ether to afford 38 g of the title compound of this Preparation 1A, mp 100-102° C. Analysis calculated for C18H16O2 : 264.1146. Found: 264.1149.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. washwashed with four portions of 10% HCl, two portions of saturated NaHCO3 solution, and one portion of brine
  4. customThe solvent was removed in vacuo
  5. customthe crude oil was triturated with diethyl ether
  6. customto afford

Sources & evidence

ORD record
ord-ae62cad4a06e4e85ab0d2863d3177125
Source dataset
uspto-grants-2000_09
Patent number
US06117874

Reaction notes

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