1-Adamantanol → 3-(1-Admantyl)-4'-iodobiphenyl-4-ol

HRID 710463Notes

Reaction equation

HRID 710463 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15]12(O)[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2>CC(O)=O.CCOC(C)=O>[C:15]12([C:10]3[CH:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=4)[CH:13]=[CH:12][C:11]=3[OH:14])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2

Participants

5

Reactant 2

HCID 641521-AdamantanolHCID 20640304-Hydroxy-4'-iodobiphenyl

Product 1

HCID 871266403-(1-Admantyl)-4'-iodobiphenyl-4-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4′-iodobiphenyl-4-ol (0.332 g, 2 mmol) and 1-admantanol (0.15 g, 0.51 mmol) in AcOH (2 ml) concentrated H2SO4 (0.5 ml) was added and the reaction mixture was stirred for 50 h at room temperature. This was diluted to 100 ml with EtOAc and washed with NaHCO3 solution, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was crystallized from MeOH to give the product (0.195 g; 93%), as a colourless paste. 1H NMR (CDCl3) 1.78 (m, 6H); 2.07 (s, 3H); 2.15 (s, 6H); 6.69 (d, 1H, J=8.15 Hz); 7.21-7.28 (m, 3H); 7.37 (d, 1H, J=2.28 Hz); 7.69 (d, 2H, J=8.45 Hz).

Workup

  1. additionwas added
  2. washwashed with NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was crystallized from MeOH
  7. customto give the product (0.195 g; 93%)

Sources & evidence

ORD record
ord-a7276908eb5d46acb1f31a4b8b789464
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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