Water → 3-Methylindene

HRID 1656356Notes

Reaction equation

HRID 1656356 reaction equation
O[C:2]1([CH3:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:11][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 5837511-Methyl-2,3-dihydro-1H-inden-1-OL

Product 1

HCID 130253-MethylindeneYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 24.64 (0.166 mol) of 1-hydroxy-1-methyl-2,3-dihydro-1H-indene and 0.30 g of p-toluenesulphonic acid monohydrate in 300 ml of toluene was heated to reflux for 3 h with water being collected by means of a Dean Stark trap. The reaction mixture was cooled, washed with water (3×100 ml), then with saturated sodium chloride solution (100 ml), dried (K2CO3) and evaporated in vacuo to leave an orange oil. This was vacuum distilled to yield 14.57 g (67%) of the title product as a colourless oil, b.p. 32°-35° C./0.3 mm of Hg. NMR δ(CDCl3) 2.17 (3H, m), 3.31 (2H, m), 6.20 (1H, m), 7.16-7.35 (3H, m), 7.45 (1H, m).

Workup

  1. customcollected by means of a Dean Stark trap
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water (3×100 ml)
  4. dry with materialwith saturated sodium chloride solution (100 ml), dried (K2CO3)
  5. customevaporated in vacuo
  6. customto leave an orange oil
  7. distillationThis was vacuum distilled

Sources & evidence

ORD record
ord-22a755d67a1a4dba8491066187c2026a
Source dataset
uspto-grants-1993_10
Patent number
US05254561

Reaction notes

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