Benzene → Methyl 4-(tetrahydropyran-2-yloxy)phenylacetate

HRID 1579045Notes

Reaction equation

HRID 1579045 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=[O:20])=CC=1.[CH:24]1C=[CH:28][CH:27]=[CH:26][CH:25]=1>>[O:20]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 21557782Methyl 4-(tetrahydropyran-2-yloxy)phenylacetate

Procedure

A mixture of 38.5 g. of methyl 4-hydroxyphenylacetate, 3.8 l. of benzene and 0.9 g. of p-toluenesulfonic acid is heated to the boiling point and about 20 ml. of solvent are distilled to remove moisture, it is then cooled to room temperature and treated with 130 ml. of freshly distilled dihydropyran. The reaction mixture is kept at room temperature for 1 hour and washed with 10% sodium bicarbonate solution and water, dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue is dissolved in methylene chloride and filtered through neutral alumina, thus obtaining the pure methyl 4-(tetrahydropyran-2-yloxy)phenylacetate.

Workup

  1. additionA mixture of 38.5 g
  2. distillationof solvent are distilled
  3. customto remove moisture, it
  4. additiontreated with 130 ml
  5. washwashed with 10% sodium bicarbonate solution and water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness under reduced pressure
  8. dissolutionThe residue is dissolved in methylene chloride
  9. filtrationfiltered through neutral alumina

Sources & evidence

ORD record
ord-5bfbb322c8dc4f3d868db611a3892eec
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

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