HCID 178519467, compound → HCID 178519466, compound

HRID 1657504Notes

Reaction equation

HRID 1657504 reaction equation
[OH:1][CH:2]([CH:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[C-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24]>[Cl-].[Ca+2].[Cl-]>[C:2]([CH:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[C-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1)(=[O:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24]

Participants

3

Reactant 1

HCID 178519467HCID 178519467, compound

Product 1

HCID 178519466HCID 178519466, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 5284359Calcium ChlorideSolvent

Procedure

1-(α-Hydroxybenzyl)-2-ferrocenyl cyclopentane (360 mg; 1 mmole) was added to a suspension of chromium trioxide dipyridine complex (1.6g; sixfold excess) in calcium chloride dried methylene chloride (25 ml) at room temperature with stirring for 1 hr. The suspension was filtered, the organic solution was washed with 2N NaOH (2 × 100 ml), 2N HCl (2 × 100 ml) and water (2 × 100 ml), and dried (Na2SO4) to yield a pale brown oil which crystallized on trituration with petroleum ether. Recrystallization from petroleum ether (bp 40°-60°) gave the desired product as a yellow solid (80 mg; 22%) mp 109°-110° IR:νmax 1670 cm-1 'HNMR: δ 7.7 and 7.4 (multiplets 5H); 4.0 (s, 5H); 4.1 - 3.9 (m; 4H); 3.5 (m, 1H); 2.0 (m; 7 H)

Workup

  1. filtrationThe suspension was filtered
  2. washthe organic solution was washed with 2N NaOH (2 × 100 ml), 2N HCl (2 × 100 ml) and water (2 × 100 ml)
  3. dry with materialdried (Na2SO4)
  4. customto yield a pale brown oil which
  5. customcrystallized on trituration with petroleum ether
  6. customRecrystallization from petroleum ether (bp 40°-60°)

Sources & evidence

ORD record
ord-bda39e085efd41a4872e484eaaca43d6
Source dataset
uspto-grants-1976_06
Patent number
US03960911

Reaction notes

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