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

HRID 1659620Notes

Reaction equation

HRID 1659620 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) dihyropyran 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-054a46ff68ef45d9a0745769c1e33f25
Source dataset
uspto-grants-1981_12
Patent number
US04304924

Reaction notes

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