4-Hydroxybenzaldehyde → 2-(Hexyloxy)benzaldehyde

HRID 846261Notes

Reaction equation

HRID 846261 reaction equation
CN([CH:4]=[O:5])C.C(=O)([O-])[O-].[K+].[K+].[OH:12][C:13]1[CH:20]=[CH:19][C:16](C=O)=[CH:15][CH:14]=1.[CH2:21](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>O>[CH2:21]([O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:19][C:20]=1[CH:4]=[O:5])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 81011-BromohexaneHCID 11430Potassium Carbonate

Product 1

HCID 1389512-(Hexyloxy)benzaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 250 ml of DMF containing 207 g of anhydrous potassium carbonate (1.5M) was added 122 g of 4-hydroxybenzaldehyde and 181.6 g of hexylbromide. The resultant mixture was heated at reflux temperature overnight after which it was poured into cold water and extracted with ethylacetate. The extracts were dried and evaporated in vacuo to afford the desired subtitled intermediate (80% yield), b.p. 110°-115° C.

Workup

  1. temperatureat reflux temperature overnight after which it
  2. extractionextracted with ethylacetate
  3. customThe extracts were dried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-15d173bb53d647d288e8eb7dc4418afe
Source dataset
uspto-grants-1992_08
Patent number
US05135955

Reaction notes

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