Monobenzone → HCID 67715504, compound

HRID 1378836Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[C:22]([O-:25])([O-])=[O:23].[K+].[K+]>CC(C)=O>[CH2:17]([O:15][C:12]1([O:23][C:22]2([O:25][CH2:11][CH2:10][CH2:9][CH2:14][CH3:13])[CH:21]=[CH:20][C:19]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:18][CH2:17]2)[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH2:13]1)[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 80 °C

Procedure

30 g (150 mmol) 4-(benzyloxy)phenol and 22.35 g 1-bromo-pentane (150 mmol) were dissolved in 250 ml acetone. The solution was heated to 80° C. and stirred with a mechanical stirrer. At this temperature, 118.5 g K2CO3 (1.09 mol) was added in one portion. The resulting heterogeneous solution was allowed to stir at 80° C. for 16 hours. The reaction was monitored by TLC until completion. Excess K2CO3 and the byproduct KBr were removed by filtration. The solution was then acidified with concentrated HCl. Evaporation of the solvent resulted in a light yellow colored oil. No further purifications were needed to obtain the 1-pentyloxy-4-(benzyloxy)phenyl ether intermediate.

Workup

stirringto stir at 80° C. for 16 hours
customExcess K2CO3 and the byproduct KBr were removed by filtration
customEvaporation of the solvent
customresulted in a light yellow colored oil

Sources & evidence

ORD record: ord-1a1846d0c68446c39f8fc9fe249d32cb
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668614

Reaction notes

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