Acetic Anhydride → Acetic acid 4-(2-phenyl-tetrahydro-pyran-2-yl)-phenyl ester

HRID 70737Notes

Reaction equation

HRID 70737 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:1]1([C:7]2([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:20](=[O:22])[CH3:21])=[CH:17][CH:18]=3)[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 167347324-(2-Phenyl-tetrahydro-pyran-2-yl)-phenol

Product 1

HCID 66968115Acetic acid 4-(2-phenyl-tetrahydro-pyran-2-yl)-phenyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(2-Phenyl-tetrahydro-pyran-2-yl)-phenol (500 mg, 2 mmol) was dissolved in pyridine (10 mL). Acetic anhydride (1 mL) was added at drop wise at 0° C. The reaction temperature was allowed to raise to room temperature. After 1 h the reaction was quenched the addition of water (5 mL). Dichloromethane (20 mL) was added. The organic phase was washed with aqueous HCl (1M, 2×10 mL), brine (10 mL), dried (Na2SO4) and concentrated in vacuo. Purified on a short column (eluent: dichloromethane). Yield: 560 mg.

Workup

  1. customAfter 1 h the reaction was quenched
  2. additionthe addition of water (5 mL)
  3. additionDichloromethane (20 mL) was added
  4. washThe organic phase was washed with aqueous HCl (1M, 2×10 mL), brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customPurified on a short column (eluent: dichloromethane)

Sources & evidence

ORD record
ord-b7adf43328c448e083678d5e27577d92
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Reaction notes

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