p-Toluenesulfonic acid → 2-[2-(4-Bromophenoxy)ethoxy]tetrahydro-2H-pyran

HRID 2198684Notes

Reaction equation

HRID 2198684 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>O.C(Cl)Cl>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:9][CH2:8][CH2:7][O:6][C:5]1[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 991682-(p-Bromophenoxy)ethanol

Product 1

HCID 128104732-[2-(4-Bromophenoxy)ethoxy]tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 12.0 g (55.4 mmol) 2-(4-bromophenoxy)ethanol, 100 ml dry methylene chloride and 5.1 g (60.9 mmol) dihydropyran is added, at RT, 0.42 g (2.2 mmol) p-toluenesulfonic acid.water. The mixture is stirred for 3 days at RT, after which 50 ml methylene chloride, 50 ml water and 10 ml aqueous 15% potassium carbonate are added. The organic phase is separated and washed with water (60 ml) and with saturated aqueous sodium chloride, and is then dried over calcium sulfate. Solvent is removed by rotary evaporation to yield 4-(2-tetrahydropyranyloxyethoxy)bromobenzene.

Workup

  1. additionis added, at RT
  2. customThe organic phase is separated
  3. washwashed with water (60 ml) and with saturated aqueous sodium chloride
  4. dry with materialis then dried over calcium sulfate
  5. customSolvent is removed by rotary evaporation

Sources & evidence

ORD record
ord-27f7c7b2f3a84af3a2bf1efea865e813
Source dataset
uspto-grants-1982_11
Patent number
US04359424

Reaction notes

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