Tetrahydrofuran → 9-(chloromethyl)-9H-xanthene

HRID 2373078Notes

Reaction equation

HRID 2373078 reaction equation
[CH:1]1[C:14]2[CH:13]([CH2:15]O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:19])=O.C1COCC1>N1C=CC=CC=1>[Cl:19][CH2:15][CH:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:6][C:5]2[C:14]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 28015919H-Xanthene-9-methanol

Product 1

HCID 184103399-(chloromethyl)-9H-xantheneYield 95.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4.0 g of 9-xanthenemethanol and 3.0 mL of freshly distilled thionyl chloride in 30 mL of freshly distilled THF was added dropwise 1.7 mL of pyridine over a period of 15 minutes. The mixture was heated in an oil bath at 50° C. for 12 hours, cooled to room temperature, and washed with half sat'd brine (30 mL), sat'd NaHCO3 (30 mL) and water (2×30 mL). The organic layer was dried over MgSO4 and the solvent was evaporated in vacuo to give 4.16 g (95.7%) of the crude 9-chloromethylxanthene as an off-white solid. Recrystallization from CH3OH--CH2Cl2 (4:1) gave 3.53g (81.35%) of the pure 9-chloromethylxanthene as white needles, m.p. 104.5°-106° C.; 1H NMR (CDCl3 ):δ 3.67 (d, 2H, CH2), 4.32 (t, 1H, CH), 7.04-7.46 (m, 8H, aryl).

Workup

  1. temperaturecooled to room temperature
  2. washwashed with half sat'd brine (30 mL), sat'd NaHCO3 (30 mL) and water (2×30 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b25153589e494201968c6e9076b22680
Source dataset
uspto-grants-1992_03
Patent number
US05101059

Reaction notes

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