Hydrochloric Acid → HCID 18994280, compound

HRID 375092Notes

Reaction equation

HRID 375092 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([C:11](=[O:18])[CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:8]=[CH:9][CH:10]=1.Cl>C1COCC1>[OH:4][C:5]1[CH:6]=[C:7]([C:11](=[O:18])[CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18994251HCID 18994251, compound

Product 1

HCID 18994280HCID 18994280, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The methyloxymethoxy group was removed by treatment of 4-[(3-methyloxymethoxyphenyl)oxomethyl]tetrahydropyran (0.82 g, 3.27 mmol), prepared as in step 2 with concentrated hydrochloric acid (2.45 mL, 0.75 mL/mmol) in THF (13 mL) at ambient temperature for 0.5 hours. The reaction mixture was partitioned between water and ethyl acetate and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide 4-[(3-hydroxyphenyl)oxomethyl]tetrahydropyran as a brown solid (0.65 g, 96%) which was used without further purification.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f03b263937d84ce2b5dd3aaa2aa92fd2
Source dataset
uspto-grants-1996_01
Patent number
US05484786

Reaction notes

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