4-tert-Butylphenol → HCID 60026695, compound

HRID 400634Notes

Reaction equation

HRID 400634 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].[CH3:12][C:13]([CH3:18])=[CH:14][C:15](Cl)=[O:16].C(N(CC)CC)C>C(OCC)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:15](=[O:16])[CH:14]=[C:13]([CH3:18])[CH3:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 8471TriethylamineHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 60026695HCID 60026695, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a chilled solution of 4-tert-butylphenol (15 g, 100 mmol) and 11.12 mL of 3-methylbut-2-enoyl chloride in 200 mL of diethyl ether at 0° C. was added 13.9 mL of triethylamine by addition funnel. The reaction mixture was warmed to room temperature and stirred until TLC indicated the reaction was complete. The reaction mixture was then filtered through diatomaceous earth, and the diethyl ether layer was washed two times with water, washed with brine, dried over magnesium sulfate, and concentrated in vacuo to leave 23 g of 3-methylbut-2-enoic acid 4-tert-butylphenyl ester as a brown oil that partially crystallized upon standing.

Workup

  1. additionby addition funnel
  2. filtrationThe reaction mixture was then filtered through diatomaceous earth
  3. washthe diethyl ether layer was washed two times with water
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c0cb6b9e6d44c5faaf2c29814ae07c2
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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