1-Indanone → HCID 68937042, compound

HRID 1808749Notes

Reaction equation

HRID 1808749 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].[Cl:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O>CO>[Cl:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=[C:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]1=[O:10]

Participants

5

Reactant 3

HCID 67351-IndanoneHCID 14798Sodium HydroxideHCID 12793355HCID 12793355, compound

Product 1

HCID 68937042HCID 68937042, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of indan-1-one (0.4 g, 3.03 mmol) and sodium hydroxide (0.6 g, 15 mmol) in methanol (25 ml) was added to the solution of 3-(3-chloropropoxy)benzaldehyde in methanol (10 ml). The resulting solution was shaken for 30 min and allowed to stand at room temperature with intermittent shaking. The completion of reaction was monitored by TLC. After the completion, excess of methanol was removed; crushed ice was added and allowed to stand overnight. The precipitates obtained were filtered, washed thoroughly with distilled water and dried. The crude product was crystallized from a mixture of acetone and petroleum ether to yield white colored crystals of 2-[3-(3-chloropropoxy)benzylidene]-indan-1-one (1) (0.21 g, 33.5%), mp 73-75° C.

Workup

  1. customto stand at room temperature with intermittent shaking
  2. customThe completion of reaction
  3. customAfter the completion, excess of methanol was removed
  4. additioncrushed ice was added
  5. waitto stand overnight
  6. customThe precipitates obtained
  7. filtrationwere filtered
  8. washwashed thoroughly with distilled water
  9. customdried
  10. customThe crude product was crystallized from a mixture of acetone and petroleum ether

Sources & evidence

ORD record
ord-5aaf5821e2bc449482bcd904e50a6f09
Source dataset
uspto-grants-2013_01
Patent number
US08361996B2

Reaction notes

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