Citric Acid → 4-(4-Bromophenyl)oxan-4-ol

HRID 1955651Notes

Reaction equation

HRID 1955651 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[O:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]2([OH:15])[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 78041,4-DibromobenzeneHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 188010634-(4-Bromophenyl)oxan-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,4-Dibromobenzene (1 17.96 g, Aldrich) in tetrahydrofuran (THF) (700 ml) was cooled to -7020 C. under nitrogen and butylithium (175 ml) was added dropwise. After stirring the mixture for 15 minutes, tetrahydro-4H-pyran4-one (25 g, Aldrich) in the THF (300 ml) was added. The reaction was left for 2 hours before being allowed to warm to room temperature. The reaction mixture was shaken with 5% citric acid (800 ml), then extracted with diethyl ether (3×600 ml). The combined organic layers were washed with water (500 ml), and dried over MgSO4. Removal of the solvent from the filtrate gave the crude tide product as an off-white solid.

Workup

  1. additionunder nitrogen and butylithium (175 ml) was added dropwise
  2. waitThe reaction was left for 2 hours
  3. extractionextracted with diethyl ether (3×600 ml)
  4. washThe combined organic layers were washed with water (500 ml)
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent from the filtrate
  7. customgave the crude tide product as an off-white solid

Sources & evidence

ORD record
ord-81d5125405e041f3899df3c940871bd6
Source dataset
uspto-grants-1998_07
Patent number
US05776951

Reaction notes

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