Water → HCID 20387074, compound

HRID 1606570Notes

Reaction equation

HRID 1606570 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].[C:17](Cl)(=[O:21])/[CH:18]=[CH:19]/[CH3:20].O>[OH-].[Na+].C(O)C.C1C=CC=CC=1>[C:17]([O:12][C:10]1[CH:11]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:7])=[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:9]=1)(=[O:21])/[CH:18]=[CH:19]/[CH3:20]

Participants

7

Reactant 3

HCID 962WaterHCID 755502,6-Di-tert-butylhydroquinoneHCID 643131trans-Crotonyl chloride

Product 1

HCID 20387074HCID 20387074, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

3,5-di tert.butyl-4-hydroxyphenyl crotonate was prepared by dissolving 22.2 grams of 2,6-di tert.butyl hydroquinone in a solution of 4 grams of sodium hydroxide in 100 milliliters of ethanol and adding drop wise to this solution a solution of 11.5 grams of crotonyl chloride in 50 milliliters of benzene. The addition was completed in 45 minutes. The reaction mixture was stirred for 4 hours at room temperature and then at 50° C. for 1 hour. After adding 100 milliliters of water to the reaction mixture, the layers were separated. The organic layer was evaporated to dryness and the residue dissolved in hexane. The hexane solution was washed three times with 10 percent sodium hydroxide solution, once with water, dried over sodium sulfate, and cooled to yield 10.5 grams of product which after recrystallization from hexane melted at 80° C. to 81.5° C.

Workup

  1. additionThe addition
  2. waitat 50° C. for 1 hour
  3. customthe layers were separated
  4. customThe organic layer was evaporated to dryness
  5. dissolutionthe residue dissolved in hexane
  6. washThe hexane solution was washed three times with 10 percent sodium hydroxide solution
  7. dry with materialonce with water, dried over sodium sulfate
  8. temperaturecooled

Sources & evidence

ORD record
ord-a4087c23a682480db0f8be9e7babf467
Source dataset
uspto-grants-1976_04
Patent number
US03953402

Reaction notes

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