Bromocyclopentane → HCID 6484666, compound

HRID 378969Notes

Reaction equation

HRID 378969 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C.O>[CH:18]1([O:1][C:2]2[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 8991o-VanillinHCID 11430Potassium Carbonate

Product 1

HCID 6484666HCID 6484666, compoundYield 615%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-hydroxy-3-methoxy-benzaldehyde (10 g, 6.57 mmoles), K2CO3 (18.16 g, 131 mmoles), cyclopentyl-bromide (14.05 ml, 131 mmoles) in absolute ethanol (150 ml) under nitrogen was refluxed under stirring for 55 hours. The mixture was diluted with water, thrice extracted in ethyl acetate, washed with water, anhydrified over Na2SO4 and evaporated to dryness, the yielded oil was purified by flash chromatography on silica gel (eluent petrolatum/ethyl acetate 95:5) to give 8.9 g of the title product (yield: 61%).

Workup

  1. temperaturewas refluxed
  2. extractionextracted in ethyl acetate
  3. washwashed with water
  4. customevaporated to dryness
  5. customthe yielded oil was purified by flash chromatography on silica gel (eluent petrolatum/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-114a80d13eb54f2fb9c1fec91ebb6b9f
Source dataset
uspto-grants-2001_10
Patent number
US06297257B1

Reaction notes

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