Hydrochloric Acid → HCID 58954783, compound

HRID 333270Notes

Reaction equation

HRID 333270 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:15]=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:17][Li].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:15]([OH:16])[CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 82132295HCID 82132295, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 58954783HCID 58954783, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3,4-dichlorophenyl)cyclohexanecarbaldehyde (440 mg, 1.71 mmol) in anhydrous THF (17 mL) at 0° C. was added slowly methyl lithium (1.6 M in Et2O, 3.21 mL, 5.14 mmol). The solution was allowed to warm to RT and was stirred for 16 h. It was then quenched with MeOH (5 mL). The crude reaction mixture was poured into 2M HCl (15 mL) and washed with EtOAc (3×20 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated to give 1-(1-(3,4-dichlorophenyl)cyclohexyl)ethanol. HPLC Rt=11.28 min; 1H NMR (400 mHz, CDCl3) 7.44-7.41 (m, 2H), 7.20 (dd, J=2.2, 8.4 Hz, 1H), 3.63-3.58 (m, 1H), 2.39-2.35 (m, 1H), 2.14-2.10 (m, 1H), 1.67-1.48 (m, 5H), 1.31-1.16 (m, 3H), 0.92 (d, J=6.6 Hz, 3H).

Workup

  1. customIt was then quenched with MeOH (5 mL)
  2. customThe crude reaction mixture
  3. washwashed with EtOAc (3×20 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-50a17aeee93347798d59374650bf46aa
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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