Hydrochloric Acid → Benzoic acid, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-, methyl ester

HRID 621833Notes

Reaction equation

HRID 621833 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Cl.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>CC(=O)OCC>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 7456MethylparabenHCID 80803,4-dihydro-2H-pyran2×

Product 1

HCID 11770459Benzoic acid, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-, methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 4-hydroxybenzoate (10 g) in EA (60 ml) containing saturated ethereal HCl (3.5 ml) was treated with dihydropyran (12 ml) and the solution was allowed to stand at room temperature for 24 h. A further quantity of dihydropyran (12 ml) and ethereal HCl (3.5 ml) was added and the solution was left for 17 h. The solvent was evaporated and the residue was dissolved in ER (100 ml) and washed with 2N NaOH solution (2×50 ml), brine (50 ml) and then dried. Evaporation gave a residue which on purification by chromatography using 3:97 ER-toluene as eluant gave the title compound as a white solid (10.2 g), m.p. 58°-62°.

Workup

  1. waitthe solution was left for 17 h
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in ER (100 ml)
  4. washwashed with 2N NaOH solution (2×50 ml), brine (50 ml)
  5. customdried
  6. customEvaporation
  7. customgave a residue which
  8. customon purification by chromatography

Sources & evidence

ORD record
ord-132cb0f249214c188fbb6d1184b8e846
Source dataset
uspto-grants-1989_04
Patent number
US04824993

Reaction notes

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