4-Hydroxybenzaldehyde → HCID 14146341, compound

HRID 375536Notes

Reaction equation

HRID 375536 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][Cl:16].O.[CH3:18]N(C)C=O>>[Cl:16][CH2:15][CH2:14][CH2:13][CH2:18][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 6228Dimethylformamide2×HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydride

Product 1

HCID 14146341HCID 14146341, compound

Conditions

Temperature
60 °C

Procedure

4-Hydroxybenzaldehyde (26.4 g) in dimethylformamide (50 mL) is added to sodium hydride (8.64 g of 60% in oil) in dimethylformamide (200 mL). 1-Bromo-3-chloropropane (93.2 g) is added and the mixture stirred at 60° C. for 3 hours. The mixture is poured into water (400 mL) and extracted with diethyl ether (3×150 mL). The extracts are dried over MgSO4, filtered and evaporated to leave an orange oil. The oil is distilled end 40.7 g of the title compound collected at 158°-175° C./0.7 mmHg as a yellow oil.

Workup

  1. extractionextracted with diethyl ether (3×150 mL)
  2. dry with materialThe extracts are dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto leave an orange oil
  6. distillationThe oil is distilled end 40.7 g of the title compound
  7. customcollected at 158°-175° C./0.7 mmHg as a yellow oil

Sources & evidence

ORD record
ord-d13fa5989791419f9a3440f9770bcdcc
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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