1-Tetralone → 1-Methyl-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 487098Notes

Reaction equation

HRID 487098 reaction equation
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[CH3:12][Mg]Br>CCOCC>[OH:10][C:9]1([CH3:12])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2][CH2:1][CH2:11]1

Participants

4

Reactant 2

HCID 107241-TetraloneHCID 178418573HCID 178418573, compound

Product 1

HCID 1398601-Methyl-1,2,3,4-tetrahydronaphthalen-1-olYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 98.0 g (0.670 mol) of α-tetralone in 800 ml of anhydrous ether was added over 30 min to a solution of 285 ml (0.855 mol) of 3.0M methyl magnesium bromide in ether under N2 whilst stirring magnetically. After completion of the addition, the reaction was heated to reflux for 30 min, allowed to cool, then quenched with 120 ml of saturated ammonium chloride solution. The ether layer was decanted from an offwhite solid, washed with water (400 ml), then with saturated sodium chloride solution, dried (K2CO3) and evaporated in vacuo to leave 91.9 g (85%) of an orange solid. NMR δ(CDCl3) 1.57 (3H, s), 1.77 (1H, s), 1.80-2.00 (4H, m), 2.80 (2H, m), 7.08 (1H, d of d), 7.18 (1H, t of d), 7.23 (1H, t of d), 7.60 (1 H, d of d).

Workup

  1. additionAfter completion of the addition
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 30 min
  4. temperatureto cool
  5. customquenched with 120 ml of saturated ammonium chloride solution
  6. customThe ether layer was decanted from an offwhite solid
  7. washwashed with water (400 ml)
  8. dry with materialwith saturated sodium chloride solution, dried (K2CO3)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-b13566e4798e4aa88f203e5ca5834069
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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