p-Toluenesulfonic acid → 6-Bromo-2,2,4,4-tetramethylchroman

HRID 395057Notes

Reaction equation

HRID 395057 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](O)=[C:4]([C:9]([CH3:16])([CH3:15])[CH2:10][C:11]([OH:14])([CH3:13])[CH3:12])[CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[O:14][C:11]([CH3:13])([CH3:12])[CH2:10][C:9]2([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 225688104-Bromo-2-(3-hydroxy-1,1,3-trimethyl-butyl)-phenol

Product 1

HCID 121370056-Bromo-2,2,4,4-tetramethylchromanYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-bromo-2-(3-hydroxy-1,1,3-trimethyl-butyl)-phenol (1.1 g, 3.92 mmol) and p-toluene sulfonic acid (0.744 g, 3.92 mmol) in benzene (20 mL) was refluxed overnight. The reaction mixture cooled to ambient temperature, filtered on silica gel and washed with 10% ethyl acetate in hexane. The filtrate and washings were evaporated in vacuo to an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent to afford the title compound as a pale yellow oil (0.84 g, 80%).

Workup

  1. filtrationfiltered on silica gel
  2. washwashed with 10% ethyl acetate in hexane
  3. customThe filtrate and washings were evaporated in vacuo to an oil which

Sources & evidence

ORD record
ord-66f6717b7d454a21a8cebed71b8681c8
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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