2-Bromo-1-(4-hydroxyphenyl)ethanone → HCID 18796348, compound

HRID 1003270Notes

Reaction equation

HRID 1003270 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 18796348HCID 18796348, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-4'-hydroxyacetophenone (860 mg) was dissolved in dichloromethane (20 ml), and 3,4-dihydro-2H-pyran (550 μl) and pyridinium p-toluenesulfonate (100 mg) were added to the solution at room temperature with stirring. After reaction for 17 hours, the reaction mixture was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1) gave 2-bromo-4'-((2RS)-2-tetrahydropyranyloxy)acetophenone (1.01 g) having a melting point of 102-104° C.

Workup

  1. customAfter reaction for 17 hours
  2. washthe reaction mixture was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-60748adbec3043f48882216ca258a2ac
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

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