4-Hydroxybenzyl Alcohol → HCID 19594010, compound

HRID 1608476Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br.[OH2:24]>CN(C)C=O>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:24][C:2]2[CH:9]=[CH:8][C:5]([CH2:10][OH:13])=[CH:4][CH:3]=2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-Hydroxybenzyl alcohol (24.82 g, 0.2 mole) was added to a stirred suspension of finely ground potassium carbonate (42.0 g, 0.4 mole) in dry dimethylformamide (250 mL). The resultant mixture was stirred at 60° C. under dry nitrogen for 10 minutes, then 1,6-dibromohexane (24.4 g, 0.1 mole) was added. The reaction mixture was maintained at 60° C. for 5 hours, then allowed to cool to room temperature and stirred for 17 hours. The reaction mixture was then poured slowly into ice/water (800 mL). A tan precipitate formed, which was collected by filtration, washed with water, and dried in air to give a sticky solid. This material was triturated with 2-propanol (100 mL) and then with cold water (200 mL), to give the desired product as a powder (13.8 g, 42% yield) which was collected by (slow and difficult) filtration. The compound melted at 96°-110° C., and its structure was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

Workup

temperatureto cool to room temperature
customA tan precipitate formed
filtrationwhich was collected by filtration
washwashed with water
customdried in air
customto give a sticky solid
customThis material was triturated with 2-propanol (100 mL)

Sources & evidence

ORD record: ord-6fdcd8deba1d4fcb8331d1ba6d9a6f55
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05395736

Reaction notes

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