4-tert-Butylphenol → HCID 16071943, compound

HRID 466184Notes

Reaction equation

HRID 466184 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>[Cu]>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([O:20][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[CH:18][CH:19]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 73934-tert-ButylphenolHCID 77304-BromoanisoleHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 16071943HCID 16071943, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
210 °C

Procedure

The starting material is prepared as follows: 4-Bromoanisole (28.06 g, 0.15 mol), 4-tert-butylphenol (27.04 g, 0.18 mol), potassium carbonate (6.9 g, 0.05 mol) and copper powder (0.2 g, 3 mmol) are combined under nitrogen and heated at 210° C. for 2.5 hours. The mixture is then cooled and treated with 1N NaOH to pH 12. Three extractions with ether are carried out. The combined extracts are dried (MgSO4) and evaporated. The residue is distilled under vacuum to yield 4-(p-tert-butylphenoxy)anisole, b.p. 220° C./20 mmHg. A mixture of the product (18.55 g, 68.5 mmol) and pyridinium hydrochloride (500 g, 4.33 mol) is heated at 230° C. for 2 hours under nitrogen, then cooled to room temperature and partitioned between water and ether. The aqueous layer is extracted with ether, the extract is dried (MgSO4) and evaporated to give 4-(p-tert-butylphenoxy)phenol as an oil. Such is converted to 5-(p-tert-butylphenoxy)salicylaldehyde, which is then converted to 3-(N-hydroxyaminomethyl)-6-(p-tert-butylphenoxy-2H-1-benzopyran as described hereinabove.

Workup

  1. customThe starting material is prepared
  2. temperatureThe mixture is then cooled
  3. extractionThree extractions with ether
  4. dry with materialThe combined extracts are dried (MgSO4)
  5. customevaporated
  6. distillationThe residue is distilled under vacuum

Sources & evidence

ORD record
ord-67db94b2aec244128ecf81d36a3f05ac
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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