Water → 1,2-Dihydro-4-methylnaphthalene

HRID 487099Notes

Reaction equation

HRID 487099 reaction equation
O[C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:12][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1398601-Methyl-1,2,3,4-tetrahydronaphthalen-1-olHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 5823271,2-Dihydro-4-methylnaphthaleneYield 139.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 101.9 g (0.628 mol) of 1-hydroxy-1-methyl-1,2,3,4-tetrahydronaphthalene and 1.3 g of p-toluenesulphonic acid monohydrate in 1.3 liters 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 (3×400 ml), then with saturated sodium chloride solution (400 ml), dried (K2CO3) and evaporated in vacuo to leave 126.4 g of brown liquid. This was vacuum distilled to yield 78.6 g (87%) of the title product as a pale yellow oil, b.p. 59°-62° C./1 mm of Hg. NMR δ(CDCl3) 2.06 (3H, m), 2.26 (2H, m), 2.76 (2H, t), 5.86 (1H, m), 7.11-7.27 (4H, m).

Workup

  1. customcollected by means of a Dean Stark trap
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water (3×400 ml)
  4. dry with materialwith saturated sodium chloride solution (400 ml), dried (K2CO3)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9fd701c8d5274f0c9a9b062236b7da92
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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