4-Hydroxybiphenyl → HCID 22878842, compound

HRID 2293007Notes

Reaction equation

HRID 2293007 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O:17][CH2:18][CH:19]1[O:24][CH:23](Br)[CH:22]([O:26]C(C)=O)[CH:21]([O:30]C(C)=O)[CH:20]1[O:34]C(C)=O)=O>CC(C)=O.[OH-].[K+]>[C@@H:23]1([O:13][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][CH:11]=2)[O:24][C@H:19]([CH2:18][OH:17])[C@H:20]([OH:34])[C@H:21]([OH:30])[C@H:22]1[OH:26]

Participants

5

Reactant 2

HCID 71034-HydroxybiphenylHCID 102932alpha-D-Galactopyranosyl bromide, tetraacetate

Product 1

HCID 22878842HCID 22878842, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14797Potassium HydroxideSolvent2×

Procedure

To a solution of p-phenylphenol (250 mg, 1.46 mmol) in acetone, 1 mL of 10N KOH was added followed by acetobromogalactose (1.8 g, 4.37 mmol). The reaction mixture was stirred overnight at room temperature. TLC analysis showed no starting material left. 10N KOH (1 mL) was added to complete deacetylation and the solution was again stirred overnight. After evaporation of acetone, the crude material was taken up in ethyl acetate and washed with 5×150 mL of water. Ethyl acetate was dried with MgSO4 and concentrated under reduced pressure to obtain a white solid which was further purified by column chromatography using 30% methanol/ethyl acetate; 1H NMR (CD3OD) δ3.56-3.91 (m, 6H), 4.89 (m, 1H), 7.15-7.57 (m,9H).

Workup

  1. waitleft
  2. waitthe solution was again stirred overnight
  3. customAfter evaporation of acetone
  4. washwashed with 5×150 mL of water
  5. dry with materialEthyl acetate was dried with MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a white solid which
  8. customwas further purified by column chromatography

Sources & evidence

ORD record
ord-e76b77cfce624f2abd8e9d78dd1e98a8
Source dataset
uspto-grants-1997_11
Patent number
US05686258

Reaction notes

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