Toluene → 3-Bromo-1,2-dihydro-7-(phenylmethoxy)naphthalene

HRID 709914Notes

Reaction equation

HRID 709914 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15](O)[CH:14]([Br:20])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>CCOC(C)=O.CCCCCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16]([CH:15]=[C:14]([Br:20])[CH2:13][CH2:12]2)=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 230872486-(Benzyloxy)-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 230874203-Bromo-1,2-dihydro-7-(phenylmethoxy)naphthaleneYield 57%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The intermediate, 6-(benzyloxy)-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol, was heated to reflux with p-toluenesulfonic acid monohydrate (0.916 g, 0.00482 mol) in toluene (300 mL, 3 mol) with a Dean-Stark tube for 1 hour, cooled to r.t., washed with saturated NaHCO3, water, brine, dried over anhydrous Na2SO4, filtered, evaporated in rotavapor to give a crude oil. Chromatograph with EtOAc:hexane (0:100 to 10:90) gave a solid product (17.29 g, 57%). 1H NMR (CHLOROFORM-d) δ: 7.30-7.49 (m, 5H), 6.85-6.96 (m, 1H), 6.76 (m, 3H), 5.06 (s, 2H), 2.87-3.00 (m, 2H), 2.67-2.83 (m, 2H). MS (M+1): 316.0.

Workup

  1. washwashed with saturated NaHCO3, water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated in rotavapor
  5. customto give a crude oil

Sources & evidence

ORD record
ord-0bda6aef97314e9baac31221bfda9c62
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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