Dimethyl Sulfoxide → 4-(4-Benzyloxyphenyl)phenol

HRID 1246219Notes

Reaction equation

HRID 1246219 reaction equation
[K].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.OC1C=CC(C2C=CC(O)=CC=2)=CC=1.[OH-].[Na+].CS(C)=O>O.C1(C)C=CC=CC=1>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 71124,4'-DihydroxybiphenylHCID 14798Sodium HydroxideHCID 696503134'-Benzyloxybiphenyl-4-ol potassium salt

Product 1

HCID 152688474-(4-Benzyloxyphenyl)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The process started with the synthesis of 4′-benzyloxybiphenyl-4-ol potassium salt. This compound was synthesized similar to the literature procedure for its preparation (Hay, A. S., Williams, H. M., Relles, Boulette, B. M., Donahue, P. B., Johnson, D. S. J. Polym. Sci. Polym. Lett. Ed. 1983, 21, 449; Hay, A. S., Williams, P. J., Relles, H. M., Boulette, B. M. J. Macromol. Sci-Chem. 1984, A21, 1065). A mixture of 4,4′-dihydroxybiphenyl (27.6 g, 100. mmol), 50% aqueous sodium hydroxide (8.00 g, 100. mmol in 16.0 mL water), 100 mL of DMSO and 100 mL of toluene was heated at reflux with a Dean Stark trap until all visible traces of water had been removed. The toluene was distilled from the system to give a homogeneous solution of 4′-benzyloxy-biphenyl-4-ol in DMSO for the next reaction. The yield was considered quantitative. 1H NMR (DMSO-d6): δ 5.08 (2H, s, >CH2), 6.70 (2H, d), 6.98 (2H, d), 7.29–7.44(9H. m). IR (neat, cm−1): 3036, 2866, 2577, 2340, 1734, 1610, 1501, 1377, 1247, 1177, 1106, 1027, 1000, 815, 747, 700.

Workup

  1. customThis compound was synthesized similar to the literature procedure for its preparation (Hay
  2. temperaturewas heated
  3. customhad been removed
  4. distillationThe toluene was distilled from the system

Sources & evidence

ORD record
ord-4e79f59411f3475caa4b2c8da8afba19
Source dataset
uspto-grants-2006_10
Patent number
US07125951B2

Reaction notes

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