Hexamethylenetetramine → 7-Hydroxy-6-methyl-2,3-dihydro-1h-indene-4-carbaldehyde

HRID 1099366Notes

Reaction equation

HRID 1099366 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[OH:11].C1N2CN3CN(C2)CN1C3.[C:22](=O)(O)[O-:23].[Na+]>FC(F)(F)C(O)=O>[OH:11][C:3]1[C:4]2[CH2:5][CH2:6][CH2:7][C:8]=2[C:9]([CH:22]=[O:23])=[CH:10][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 884735-Methylindan-4-olHCID 516892Sodium Bicarbonate

Product 1

HCID 230311827-Hydroxy-6-methyl-2,3-dihydro-1h-indene-4-carbaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
87.5 °C

Procedure

To a clear solution of 5-Methyl-indan-4-ol (6 gm, 0.0405 mole) in 30 ml Trifluoroacetic acid, Hexamine (5.7 gm, 0.0405 mole) was added at 25-28° C. The reaction mixture was heated and stirred at 85-90° C. for 6 hours. The cooled reaction mixture was poured into saturated Sodium bicarbonate solution and extracted with Ethylacetate (2×200 ml). The organic layer was dried over Sodium sulphate and distilled under vacuum to give a crude product which was purified by column chromatography using Ethyl acetate:Hexane (10:90) as mobile phase The collected fractions were distilled to give 5.4 gm of desired product as a solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. customThe cooled reaction mixture
  3. extractionextracted with Ethylacetate (2×200 ml)
  4. dry with materialThe organic layer was dried over Sodium sulphate
  5. distillationdistilled under vacuum
  6. customto give a crude product which
  7. customwas purified by column chromatography
  8. distillationwere distilled

Sources & evidence

ORD record
ord-de1b957f8adb482fb6152cf209b7325e
Source dataset
uspto-grants-2012_03
Patent number
US08143424B2

Reaction notes

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