p-Toluenesulfonic acid → 2-(4-Methoxy-alpha-cumyl)-4-tert-butylphenol

HRID 1281056Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([CH3:31])=[CH2:30])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([C:9]2[CH:10]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:6]=[CH:7][C:8]=2[OH:11])([CH3:31])[CH3:30])=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a three-necked 500 mL flask equipped with a mechanical stirrer, 37 g of 4-tert-butylphenol, 100 mL of toluene and 2.4 g of p-toluenesulfonic acid are charged and heater to 55° C. The 4-methoxy-α-methylstyrene (40 g) prepared in Example 1 is added over 2.5 hours. The reaction mass is stirred for an additional three hours at 65° C. The reaction mass is then washed twice with 200 mL of saturated sodium bicarbonate solution and thrice with 100 mL of water. The solvent is removed by vacuum distillation and unreacted phenol and alkene are moved by Kugelrohr distillation at 100° C./0.16 mm Hg. The title compound is prepared in a yield of 78 g as a light brown oil whose structure is consistent with 1Hnmr and mass spectroscopy.

Workup

customTo a three-necked 500 mL flask equipped with a mechanical stirrer
customto 55° C
washThe reaction mass is then washed twice with 200 mL of saturated sodium bicarbonate solution and thrice with 100 mL of water
customThe solvent is removed by vacuum distillation and unreacted phenol and alkene
distillationare moved by Kugelrohr distillation at 100° C./0.16 mm Hg

Sources & evidence

ORD record: ord-4868a1f3fc6043a987ba29bd89cc0889
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451887B1

Reaction notes

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