Water → 4-Benzyloxy-3-cyclopentyloxybenzaldehyde

HRID 1584945Notes

Reaction equation

HRID 1584945 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.C(=O)([O-])[O-].[K+].[K+].[CH:24]1(Br)[CH2:28][CH2:27][CH2:26][CH2:25]1.O>CN(C)C=O.C(OCC)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:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Product 1

HCID 211878994-Benzyloxy-3-cyclopentyloxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 4-benzyloxy-3-hydroxybenzaldehyde (60.9 g; that is prepared as described in Reference Example 36) in dry dimethylformamide (270 mL) under nitrogen is treated portionwise with potassium carbonate (79.5 g). After stirring at room temperature for 45 minutes, it is treated with cyclopentyl bromide (34.3 mL), and the resulting suspension is heated at 60° C. for 8 hours. After cooling, the solution is evaporated to low bulk under reduced pressure, to give an oil. This oil is treated with water (250 mL) and diethyl ether (300 mL), and the aqueous layer is washed with further quantities of diethyl ether (2×50 mL). The combined ethereal extracts are washed with brine (1×50 mL) and with water (3×50 mL), dried over magnesium sulfate and evaporated. The resulting residue is crystallized from methanol, to give 4-benzyloxy-3-cyclopentyloxybenzaldehyde (79 g), m.p. 55-56° C. [Elemental analysis: C,77.1; H,6.9%; calculated: C,77.0; H,6.8%].

Workup

  1. customthat is prepared
  2. temperaturethe resulting suspension is heated at 60° C. for 8 hours
  3. temperatureAfter cooling
  4. customthe solution is evaporated to low bulk under reduced pressure
  5. customto give an oil
  6. washthe aqueous layer is washed with further quantities of diethyl ether (2×50 mL)
  7. washThe combined ethereal extracts are washed with brine (1×50 mL) and with water (3×50 mL)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe resulting residue is crystallized from methanol

Sources & evidence

ORD record
ord-55c51c21cdbb46d9b29501ce5c27ee45
Source dataset
uspto-grants-1999_08
Patent number
US05935978

Reaction notes

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