(1,1'-Biphenyl)-2-ol → HCID 18786178, compound

HRID 1107936Notes

Reaction equation

HRID 1107936 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22]>C(Cl)Cl>[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([C:15]1[CH:16]=[C:11]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:12]([OH:17])=[CH:13][CH:14]=1)=[O:22]

Participants

5

Reactant 3

HCID 7017(1,1'-Biphenyl)-2-olHCID 691102-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18786178HCID 18786178, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

At ambient temperature, to a stirred suspension of aluminum chloride (2.0 g, 15.0 mmol) in CH2Cl2 (20 mL) was added 2-phenylphenol (1.28 g, 7.53 mmol). After 30 min, the reaction was cooled to 0° C. To the reaction was added dropwise a solution of 2-chlorobenzoyl chloride (0.94 mL, 7.42 mmol) in CH2Cl2 (20 mL). The reaction was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched into crushed ice (100 g) diluted with sat. aq. KH2PO4 (100 mL) and extracted with CH2Cl2. The organic extracts were dried (Na2SO4) and concentrated. The crude product was purified on Biotage KP-Sil eluting with a 3 & 10% EtOAc/pet. ether step gradient to give 0.5g (21%) of the title compound as an off white solid, mp 194-198° C. 1H NMR (DMSO-d6) δ 7.07 (dd, 1H), 7.33 (tt, 1H), 7.40 (tt, 2H), 7.46-7.49 (m, 4H), 7.51-7.59 (m, 4H), 10.8 (s, 1H). mass spectrum (EI) m/z 308 (M+).

Workup

  1. temperatureto warm to ambient temperature
  2. customThe reaction was quenched
  3. custominto crushed ice (100 g)
  4. additiondiluted with sat. aq. KH2PO4 (100 mL)
  5. extractionextracted with CH2Cl2
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified on Biotage
  9. washKP-Sil eluting with a 3 & 10% EtOAc/pet. ether step gradient

Sources & evidence

ORD record
ord-b5fcc95d0a584187b40bef2a89a6fa6d
Source dataset
uspto-grants-2000_05
Patent number
US06063815

Reaction notes

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