Iodine → alpha-(3-Cyclopentyloxy-4-methoxyphenyl)benzylalcohol
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].II.[CH:11]1([O:16][C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=2[O:25][CH3:26])[CH:20]=[O:21])[CH2:15][CH2:14][CH2:13][CH2:12]1.[NH4+].[Cl-]>C1COCC1>[CH:11]1([O:16][C:17]2[CH:18]=[C:19]([CH:20]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[OH:21])[CH:22]=[CH:23][C:24]=2[O:25][CH3:26])[CH2:12][CH2:13][CH2:14][CH2:15]1Participants
Conditions
- Temperature
- 0 °C
Procedure
A Grignard complex was formed with bromobenzene (18.84 g), magnesium, turnings (2.9 g), iodine (catalytic amount) and aluminum (catalytic amount) in THF (105 ml). A solution of bromobenzene in THF (100 ml) was added dropwise, under N2 flow, to a stirs solution of magnesium, turnings and iodine in THF (5 ml). The reaction mixture was stirred and heated. After all bromobenzene was added, the reaction mixture was stirred and refluxed for 1 hour. The mixture was cooled on an ice-bath. A solution of 3-(cyclopentyloxy)-4-methoxybenzaldehyde (22.03 g) in THF (80 ml) was added dropwise at 0° C. The reaction mixture was stirred for 2 hours at RT, then cooled to 0° C. A saturated NH4Cl solution (200 ml) was added dropwise and this mixture was extracted twice with CH2Cl2 (100 ml). The separated organic layer was dried (MgSO4), filtered and the solvent evaporated, yielding 29.3 g (98%) of (±)-3-(cyclopentyloxy)-4-methoxy-α-phenylbenzenemethanol (interm. 6).
Workup
- temperatureheated
- stirringthe reaction mixture was stirred
- temperaturerefluxed for 1 hour
- temperatureThe mixture was cooled on an ice-bath
- stirringThe reaction mixture was stirred for 2 hours at RT
- extractionthis mixture was extracted twice with CH2Cl2 (100 ml)
- dry with materialThe separated organic layer was dried (MgSO4)
- filtrationfiltered
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-2b52cc22c0674bdea603e38d8535f13c
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05952510
Reaction notes
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