Water → 5-Methyl-2-(8-phenyloctyloxy)-1,3-benzenedicarboxaldehyde

HRID 22429

Reaction equation

HRID 22429 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:26]=[O:27])[C:20]([OH:25])=[C:21]([CH:23]=[O:24])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:16][C:17]1[CH:18]=[C:19]([CH:26]=[O:27])[C:20]([O:25][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:21]([CH:23]=[O:24])[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 817442,6-Diformyl-4-methylphenolHCID 563758(8-Bromooctyl)benzene

Product 1

HCID 199302605-Methyl-2-(8-phenyloctyloxy)-1,3-benzenedicarboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

8-Phenyloctyl bromide (2.69 g, 10 mmol) was added to a stirred mixture of 5-methyl-2-hydroxy-1,3-benzenedicarboxaldehyde (1.64 g, 10 mmol) and anhydrous potassium carbonate (1.38 g, 10 mmol) in dry dimethylformamide (20 ml) at room temperature under nitrogen. The suspension was heated to 80° C. for 3 hours then allowed to cool. Water (40 ml) was added and the mixture extracted with diethyl ether (2×40 ml). The extracts were dried, filtered and evaporated to a yellow solid. Recrystallisation from methanol (25 ml) gave the title product as pale yellow crystals, m.p. 59° C.

Workup

  1. temperatureto cool
  2. extractionthe mixture extracted with diethyl ether (2×40 ml)
  3. customThe extracts were dried
  4. filtrationfiltered
  5. customevaporated to a yellow solid
  6. customRecrystallisation from methanol (25 ml)

Sources & evidence

ORD record
ord-c98a8881a4794c408626888262f8759e
Source dataset
uspto-grants-1995_06
Patent number
US05428065

Linked notes

Loading…