Hydrochloric Acid → 1-(4-Benzyloxy-phenyl)-2-ethyl-4-hydroxymethyl-3-methyl-cyclohexanol

HRID 351439

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:21]([CH:23]1[CH:28]([CH3:29])[CH:27]([CH2:30][O:31][Si](C)(C)C)[CH2:26][CH2:25][C:24]1=[O:36])[CH3:22].Cl>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:24]2([OH:36])[CH2:25][CH2:26][CH:27]([CH2:30][OH:31])[CH:28]([CH3:29])[CH:23]2[CH2:21][CH3:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

1-Benzyloxy4-iodo-benzene (5.70 g, 18.37 mmol) was dissolved in anhydrous THF (36 mL) at −10° C. Isopropyl magnesium chloride (1.0 M, 18.37 mL) was added and the mixture was stirred for 3 h. A solution of 2-ethyl-3-methyl-4-trimethylsilanyloxymethyl-cyclohexanone (12.0 g in 50 mL THF) was added slowly over 30 min by syringe pump. The reaction mixture was stirred for 30 min at 25° C. and then refluxed for 30 min. The reaction mixture was then cooled to 25° C., HCl (1.0 N, 80 mL) was added slowly, followed by addition of ethyl acetate (100 mL). The organic layer was washed with H2O (100 mL), dried over MgSO4 and purified on SiO2 (10˜15% ethyl acetate/hexane) to yield 1-(4-benzyloxy-phenyl)-2-ethyl-4-hydroxymethyl-3-methyl-cyclohexanol.

Workup

stirringThe reaction mixture was stirred for 30 min at 25° C.
temperaturerefluxed for 30 min
washThe organic layer was washed with H2O (100 mL)
dry with materialdried over MgSO4
custompurified on SiO2 (10˜15% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-c3d8936c17564bbeb3e9057aa27ba592
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183445B2

Linked notes

Loading…