Water → HCID 86733319, compound

HRID 1606571Notes

Reaction equation

HRID 1606571 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:26])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.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:26])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 962WaterHCID 660233-Phenylprop-2-enoyl chlorideHCID 755502,6-Di-tert-butylhydroquinone

Product 1

HCID 86733319HCID 86733319, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

3,5-di tert. butyl-4-hydroxyphenyl cinnamate 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 18.2 grams of cinnamoyl chloride in 50 milliliters of benzene. The addition was completed in 30 minutes and the reaction mixture was stirred for an additional 45 minutes. The reaction mixture was then poured into 150 milliliters of water and the layers were separated. The organic layer was washed three times with 10 per cent sodium hydroxide solution, once with water, dried over sodium sulfate, and then evaporated to dryness. The residue, after washing with cold hexane, yielded 10 grams of product which after recrystallization from hexane melted at 123.5° C. to 125.5° C.

Workup

  1. additionThe addition
  2. customthe layers were separated
  3. washThe organic layer was washed three times with 10 per cent sodium hydroxide solution
  4. dry with materialonce with water, dried over sodium sulfate
  5. customevaporated to dryness
  6. washThe residue, after washing with cold hexane

Sources & evidence

ORD record
ord-350daedba754489e958f7170afc6d352
Source dataset
uspto-grants-1976_04
Patent number
US03953402

Reaction notes

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