Water → Naphthalene

HRID 1522317Notes

Reaction equation

HRID 1522317 reaction equation
[CH3:1][CH2:2][C:3]([O-])(C)[CH3:4].[K+].O.[CH3:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[CH:11]1[C:10]2[C:1](=[CH:2][CH:3]=[CH:4][CH:9]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8058HexaneHCID 23683543Potassium t-amylate

Product 1

HCID 931Naphthalene

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To the suspension of ethyl triphenyl phosphonium bromide (5.69 g, 15.3 mmol) in anhydrous THF (30 ml), a solution is added by drops of potassium tert-amylate (8.7 ml, 14.7 mmol, 1.7 M solution in toluene) using a syringe at room temperature. After 1 hour, the reaction mixture is cooled to a temperature of 0° C., the solution of crude aldehyde previously obtained is added (3.32 g, 11.79 mmol) in THF (10 ml), and mixing is continued for hours at room temperature. Then, water (1 ml) is added, and dilution takes place with n-hexane (30 ml). The sediment created is filtered, and the residue is chromatographed on silica gel (cyclohexane), obtaining naphthalene derivative with formula 25 in the form of a yellow oil (3.12 g, 90%).

Workup

  1. customat room temperature
  2. customthe solution of crude aldehyde previously obtained
  3. additionmixing
  4. waitis continued for hours at room temperature
  5. filtrationThe sediment created is filtered
  6. customthe residue is chromatographed on silica gel (cyclohexane)

Sources & evidence

ORD record
ord-70672300123c45a2a37ddc77fda4da16
Source dataset
uspto-grants-2015_07
Patent number
US09074028B2

Reaction notes

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