Propylene Oxide → 1-[4-(3-Fluorophenoxy)phenoxy]propan-2-ol

HRID 1732157Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH2:16]1[O:19][CH:17]1[CH3:18].C(N(CC)CC)C>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:16][CH:17]([OH:19])[CH3:18])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6.13 g of p-(m-fluorophenoxy)phenol, 2.79 g of propylene oxide and 0.12 g of triethylamine is stirred at 90° C. for 18 hours. The cooled mixture is subsequently diluted with 100 ml of diethyl ether and washed successively twice with 50 ml of 2N hydrochloric acid each time, three times with 50 ml of 2N sodium hydroxide each time, with 50 ml of water and with 50 ml of saturated sodium chloride solution. After drying over anhydrous sodium sulfate and evaporation there is obtained 1-[p-(m-fluorophenoxy)phenoxy]-2-propanol of melting point 37°-39° C.

Workup

washwashed successively twice with 50 ml of 2N hydrochloric acid each time, three times with 50 ml of 2N sodium hydroxide each time
dry with materialAfter drying over anhydrous sodium sulfate
customevaporation there

Sources & evidence

ORD record: ord-7d78d94e419c4f73b0189b78574d9a05
Source dataset: uspto-grants-1986_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04625048

Reaction notes

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