Nitroethane → 8-Decen-3-ol, 5,9-dimethyl-2-nitro-

HRID 970281Notes

Reaction equation

HRID 970281 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=[O:2].[CH3:6][C:7](=[CH:9][CH2:10][CH2:11][CH:12]([CH2:14][CH:15]=[O:16])[CH3:13])[CH3:8]>ClCCl>[CH3:13][CH:12]([CH2:11][CH2:10][CH:9]=[C:7]([CH3:8])[CH3:6])[CH2:14][CH:15]([OH:16])[CH:4]([N+:1]([O-:3])=[O:2])[CH3:5]

Participants

4

Reactant 2

HCID 6587NitroethaneHCID 7794Citronellal

Product 1

HCID 110642298-Decen-3-ol, 5,9-dimethyl-2-nitro-Yield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nitroethane (7.5 g) was added to a stirred solution of 13.82 g of citronellal in dichloromethane. Approximately 12-14 g of Amberlyst A-21 ion exchange resin was added, and the mixture was stirred at room temperature overnight. After filtration, the resin was rinsed 4 times with 75 mL of dichloromethane. The filtrate was dried over anhydrous MgSO4 and the solvent was removed by rotary evaporation, affording 20.1 g (95%) of a mixture of stereoisomers of the desired nitro alcohol 6. 1H NMR δ (ppm) 5.2 (t, C═CH), 4.4 (m, CH3CHNO2), 2.5 (broad s, CHOH), 2.0 (br m, ═CHCH2), 1.60 and 1.65 (both s, CH3C(CH3)═), 1.5 (d, CH3CHNO2), 1.2-1.5 (m, CH2CH(CH3)CH2), 0.95 (d, CH2CH(CH3)CH2).

Workup

  1. additionApproximately 12-14 g of Amberlyst A-21 ion exchange resin was added
  2. filtrationAfter filtration
  3. washthe resin was rinsed 4 times with 75 mL of dichloromethane
  4. dry with materialThe filtrate was dried over anhydrous MgSO4
  5. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-5d1937013a9349a39f25e27ee34ab82e
Source dataset
uspto-grants-2007_12
Patent number
US07312191B2

Reaction notes

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