4-Hydroxybenzaldehyde → p-(4'-n-Butylbenzoyloxy)benzaldehyde

HRID 2050138Notes

Reaction equation

HRID 2050138 reaction equation
[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.C1C=CC=CC=1.N1C=CC=CC=1>O>[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:14][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)=[O:10])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 241BenzeneHCID 1049PyridineHCID 1200494-Butylbenzoyl chloride

Product 1

HCID 5231030p-(4'-n-Butylbenzoyloxy)benzaldehydeYield 916%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-n-Butylbenzoyl chloride (39, 2 g, 0.2 m) was added dropwise to a solution of 4-hydroxybenzaldehyde (24.4 g), (0.2 m) anhydrous benzene (320 ml) and dry pyridine (30 ml) with stirring. After completion of addition stirring was continued for 24 hours at room temperature. The resulting reaction mixture was poured into cold water. The organic layer was separated and washed with diluted hydrochloric acid solution, diluted potassium hydroxide solution and water, then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was crystallized from ethanol to yield p-(4'-n-butylbenzoyloxy)benzaldehyde (26.3 g, 46%) mp 49.7° C.

Workup

  1. additionAfter completion of addition
  2. stirringstirring
  3. customThe resulting reaction mixture
  4. customThe organic layer was separated
  5. washwashed with diluted hydrochloric acid solution, diluted potassium hydroxide solution and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-c6211577384749ac87e0967df1217f95
Source dataset
uspto-grants-1980_04
Patent number
US04200580

Reaction notes

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