Benzaldehyde → HCID 383402, compound

HRID 346027Notes

Reaction equation

HRID 346027 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[K+].Cl>C(O)C.O>[CH:13](=[C:8]1[CH2:7][C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]1=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 3340366-Methoxy-1-Indanone

Product 1

HCID 383402HCID 383402, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a 0° C. mixture of 9.66 g (59.6 mmol) of 6-methoxy-1-indanone and 6.32 g (59.6 mmol) of benzaldehyde in 10 ml ethanol was added 9.66 ml of a 4% KOH in ethanol solution. The reaction was stirred 1 hour and then added to 300 ml water and the pH of the quench adjusted to 2 with 1N hydrochloric acid. The resultant mixture was extracted with 3×300 ml ether, and the extracts combined, dried over MgSO4, evaporated and the residue triturated with ether to yield 10.8 g (72%) of present title compound as a solid. 1 -NMR(CDCl3, 300 MHz)delta(ppm): 3.80 (s, OCH3), 3.92 (s, CH2), 7.13 (dd, J=8, 2 Hz, ArH), 7.35 (m, 4ArH and vinyl H) and 7.6 (m, 3ArH).

Workup

  1. extractionThe resultant mixture was extracted with 3×300 ml ether
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customthe residue triturated with ether

Sources & evidence

ORD record
ord-9aafa250dc3741578b6301071738496e
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Reaction notes

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