4-tert-Butylphenol → HCID 22759343, compound

HRID 329289Notes

Reaction equation

HRID 329289 reaction equation
[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]1[O:21][CH2:20]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12])(=[O:3])[CH3:2].[C:22]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].[OH-].[Na+]>O.O1CCCC1>[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([OH:21])[CH2:20][O:32][C:29]1[CH:30]=[CH:31][C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:27][CH:28]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 73934-tert-ButylphenolHCID 14798Sodium HydroxideHCID 22759269HCID 22759269, compound

Product 1

HCID 22759343HCID 22759343, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of ethyl 8-acetyl-12,13-epoxytridecanoate (14.9 g., 0.05 mole), 4-tert-butylphenol (11.2 g., 0.075 mole), sodium hydroxide (7.0 g., 0.175 mole), water (30 ml.) and tetrahydrofuran (200 ml.) is stirred 4 hours at 40°-45°, 17 hours at 25° and one hour on the steam bath letting the tetrahydrofuran slowly boil away. The residue is treated with water and extracted with ether. The aqueous solution is acidified with hydrochloric acid. The oily product is taken up in ether. The ether is evaporated and the residue treated with a solution of 16.8 g. sodium bicarbonate in 275 ml. of water. The resulting solution is extracted twice with ether to remove the excess weakly acidic phenol. The aqueous solution is acidified, the product taken up in ether, washed with water and dried over sodium sulfate. The ether is evaporated leaving 10.2 g. of the crude title compound as a yellow viscous oil.

Workup

  1. extractionextracted with ether
  2. customThe ether is evaporated
  3. additionthe residue treated with a solution of 16.8 g
  4. extractionThe resulting solution is extracted twice with ether
  5. customto remove the excess weakly acidic phenol
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customThe ether is evaporated
  9. customleaving 10.2 g

Sources & evidence

ORD record
ord-624b5627838a4197af645ab138d02873
Source dataset
uspto-grants-1977_04
Patent number
US04020177

Reaction notes

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