Bromocyclopentane → 4-Benzyloxy-3-cyclopentyloxybenzaldehyde

HRID 1819335Notes

Reaction equation

HRID 1819335 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Product 1

HCID 211878994-Benzyloxy-3-cyclopentyloxybenzaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-benzyloxy-3-hydroxybenzaldehyde (5 g, 21.9 mmol) in DMF (50 mL) was added cyclopentyl bromide (4.7 mL, 43.8 mmol) and K2CO3 (12.1 g, 87.6 mmol). The reaction mixture was stirred at r.t. overnight. K2CO3 was then filtered from the mixture. The mixture was extracted with EtOAc, and the organic layer was washed with water (2×) and then brine, and finally dried over Na2SO4. The product was concentrated under reduced pressure and purified by silica gel to provide a colorless oil which solidified to a white solid upon standing. Yield: 98%.

Workup

  1. filtrationK2CO3 was then filtered from the mixture
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with water (2×)
  4. dry with materialbrine, and finally dried over Na2SO4
  5. concentrationThe product was concentrated under reduced pressure
  6. custompurified by silica gel
  7. customto provide a colorless oil which

Sources & evidence

ORD record
ord-6e9a0a0cb52d43a39374139719293b6c
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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