Formaldehyde → 2-(2-Methoxy-6-nitrophenyl)-1-ethanol

HRID 1582436Notes

Reaction equation

HRID 1582436 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12].C=O.C[C:16](C)([O-:18])C.[K+].C1COCC1>CS(C)=O.O.C(OCC)(=O)C>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH2:1][CH2:16][OH:18]

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 785542-Methyl-3-nitroanisoleHCID 66863523KOtBu THF

Product 1

HCID 227203652-(2-Methoxy-6-nitrophenyl)-1-ethanolYield 71%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a dry 25 mL flask 0.17 mg (1.0 mmol) of 2-methyl-3-nitroanisole is combined with 30 mg (0.97 mmol) paraformaldehyde in 7 mL of dimethylsulfoxide (sure-seal). This solution is treated with 1M Potassium t-butoxide/THF (0.20 mL) with the reaction mixture becoming bright red in color. After 2 hours the reaction mixture is diluted with water and ethyl acetate is added. The layers are separated followed by two ethyl acetate extractions. The organics are combined, washed with brine, dried over MgSO4, filtered, and concentrated to give a crude yellow oil that solidifies overnight. This material is purified by LC (45% ethyl acetate/heptane) to yield 140 mg (71%) of 2-(2-methoxy-6-nitrophenyl)-1-ethanol as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ2.90 (t, J=7 Hz, 2H), 3.50 (q, J=7 Hz, 2H), 3.88 (s, 3H), 4.74 (t, J=5 Hz, 1H), 7.32 (dd, J=2, 8 Hz, 1H), 7.46-7.36 (m, 2H); 13C NMR (75 MHz, CDCl3) δ158.5, 127.8, 116.2, 114.2, 62.0, 56.3, 29.2; IR (drift) 1536, 1469, 1458, 1352, 1279, 1266, 1217, 1065, 1040, 1031, 1014, 895, 806, 796, 740 cm−1.

Workup

  1. additionis added
  2. customThe layers are separated
  3. extractionfollowed by two ethyl acetate extractions
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude yellow oil
  9. customThis material is purified by LC (45% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-a0ac60fa45974f05ae0a5532af8fcbfa
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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