Toluene → HCID 86648189, compound

HRID 1047476Notes

Reaction equation

HRID 1047476 reaction equation
CO[CH:3]1[C:11]2[C:6](=[C:7]([CH2:14][CH2:15][C:16]3(O)[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)[C:8]([CH3:13])=[C:9]([CH3:12])[CH:10]=2)[CH2:5][CH:4]1[CH3:26].C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>>[CH2:24]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:16]1[CH2:15][CH2:14][C:7]1[C:8]([CH3:13])=[C:9]([CH3:12])[CH:10]=[C:11]2[C:6]=1[CH2:5][C:4]([CH3:26])=[CH:3]2

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 59608931HCID 59608931, compound

Product 1

HCID 86648189HCID 86648189, compound

Procedure

To a hot (110° C.) solution of 6.0 g (18.61 mmol) of 2-[2-(1-methoxy-2,5,6-trimethyl-2,3-dihydro-1H-inden-4-yl)ethyl]indan-2-ol in 130 ml of toluene 0.708 g (3.72 mmol) of TsOH*H2O was added. This mixture was refluxed with a Dean-Stark trap for 30 min, and then passed through short column with Silica Gel 60 (40-63 um, d 80 mm, l 60 mm). The column was additionally washed with 300 ml of toluene. The combined elute was evaporated to dryness. The product was isolated by flash chromatography using a short column with Silica Gel 60 (40-63 um, d 60 mm, l 70 mm; eluent: hexanes/ether=50/1). Yield 4.58 g (82%).

Workup

  1. temperatureThis mixture was refluxed with a Dean-Stark trap for 30 min
  2. washThe column was additionally washed with 300 ml of toluene
  3. washThe combined elute
  4. customwas evaporated to dryness
  5. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-7abffe9df4d547b4a3e884409b53e4bb
Source dataset
uspto-grants-2013_10
Patent number
US08569532B2

Reaction notes

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