Pyridine → HCID 14039202, compound

HRID 2068497Notes

Reaction equation

HRID 2068497 reaction equation
[CH3:1][C:2]([OH:16])([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)[CH3:3].N1C=CC=CC=1.[C:23]1([O:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:30](=[O:31])([O:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[O:16][C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 118654[1,1'-Biphenyl]-4-methanol, .alpha.,.alpha.-dimethyl-

Product 1

HCID 14039202HCID 14039202, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-biphenyl)-2-propanol (53 g, 250 mmol) in dry CH2Cl2 (250.0 mL) was added pyridine (24.6 mL, 305 mmol) and phenylchloroformate (35.0 mL, 280 mmol) in CH2Cl2 (125.0 mL) at −5° C. After addition forms a thick precipitate, which, after the reaction mixture is allowed to stand overnight at 0° C. is mostly dissolved. The mixture is poured onto ice and diluted with CH2Cl2 (1000 mL). The organic phase is separated and washed three times with cold water. After drying over Na2SO4 the organic layer is evaporated at reduced pressure at a bath temp of <30° C. The crystalline residue is dissolved in diethyl ether (1000 mL) and the solution is then concentrated with a stream of nitrogen at atmospheric pressure at bath temperature of 60° C. to approximately 200 mL and then rapidly cooled to 0° C. to produce a pure crystalline product 55.0 g (66% yield).

Workup

  1. additionAfter addition forms a thick precipitate, which
  2. dissolutionis mostly dissolved
  3. additionThe mixture is poured onto ice
  4. customThe organic phase is separated
  5. washwashed three times with cold water
  6. dry with materialAfter drying over Na2SO4 the organic layer
  7. customis evaporated at reduced pressure at a bath temp of <30° C
  8. dissolutionThe crystalline residue is dissolved in diethyl ether (1000 mL)
  9. concentrationthe solution is then concentrated with a stream of nitrogen at atmospheric pressure at bath temperature of 60° C. to approximately 200 mL

Sources & evidence

ORD record
ord-4b5b08b1a56945a5a4e3460c0f730aeb
Source dataset
uspto-grants-2012_10
Patent number
US08299051B2

Reaction notes

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