Formaldehyde → [2-(Propan-2-yl)phenyl]methanol

HRID 736027Notes

Reaction equation

HRID 736027 reaction equation
[Li]C(C)(C)C.I[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([CH3:15])[CH3:14].[CH2:16]=[O:17].[NH4+].[Cl-]>C1COCC1>[CH:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:16][OH:17])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 87931o-IodocumeneHCID 178418306HCID 178418306, compound

Product 1

HCID 15269897[2-(Propan-2-yl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1.7M tert-BuLi (26 ml, 44 mmol) dropwise, at −78° C. under inert atmosphere, to a solution of 1-Iodo-2-iso-propylbenzene (5 g, 20.3 mmol) in 70 ml of dry THF and stir. After 10 min, add Paraformaldehyde (2 g, 66.7 mmol) in a single portion. Stir the reaction at this temperature for 15 min and then at room temperature for 2 h. Add a saturated aqueous solution of NH4Cl and extract with CH2Cl2 three times. Dry the combined organic extracts over Na2SO4, filter and concentrate under reduced pressure to give a residue. Purify the residue by column chromatography on silica gel eluting with CH2Cl2 to afford pure (2-Isopropyl-phenyl)-methanol as pale purple oil. Add aqueous concentrated HBr (15 ml) to a solution of (2-Isopropyl-phenyl)-methanol (1,93 g, 12.85 mmol) in CH2Cl2(15 ml) and stir at room temperature. After 2 h. separate phases and wash the organic one with H2O; dry over Na2SO4 and evaporate at vacuum to obtain a residue. Purify the residue by column chromatography on silica gel eluting with CH2Cl2 to obtain 1-Bromomethyl-2-isopropyl-benzene as very pale pink light oil. 1H-NMR (CDCl3, 200 MHz): δ 7.33-7.25 (m, 3H), 7.19-7.11 (m, 1H), 4.58 (s, 1H), 3.31 (sep, J=6.8 Hz, 1H), 1.30 (d, J=6.8 Hz, 6H).

Workup

  1. customthe reaction at this temperature for 15 min
  2. waitat room temperature for 2 h
  3. extractionextract with CH2Cl2 three times
  4. dry with materialDry the combined organic extracts over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. customPurify the residue by column chromatography on silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-2450d047cbd04949b429073b2f5cec5b
Source dataset
uspto-grants-2009_09
Patent number
US07595315B2

Reaction notes

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