Benzene, 1-(chloromethyl)-2-fluoro- → HCID 20364964, compound
Reaction equation
[Cl:1][CH2:2][CH:3]1[O:8][CH2:7][CH:6]([OH:9])[CH2:5][O:4]1.[H-].[Na+].[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Cl>>[Cl:1][CH2:2][CH:3]1[O:8][CH2:7][CH:6]([O:9][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[F:12])[CH2:5][O:4]1Participants
4
Procedure
By the method of Example 43, 2-chloromethyl-5-hydroxy-1,3-dioxane was reacted with sodium hydride and o-fluorobenzyl chloride to yield 2-chloromethyl-5-(2-fluorobenzyloxy)-1,3-dioxane. This mixture of isomers was distilled using a short path distillation apparatus at 0.1 mm to obtain three fractions. Fraction 1, b.p. 95°-100°/0.1 mm was found by VPC analysis to be 3.8% cis-2-chloromethyl-5-(2-fluorobenzyloxy)-1,3-dioxane (the remainder in each case being the trans isomer). Fraction 2, b.p. 98°-102°/0.1 mm was 13.8% cis isomer. Fraction 3, b.p. 165°-170°/0.1 mm was 99% cis and solidified on standing; the solid was sublimed to a solid, m.p. 60°-62°, which was found by nmr analysis to 94% cis isomer and 6% trans isomer.
Sources & evidence
- ORD record
- ord-9fdeb00bca964375988b33ea8dfb10f6
- Source dataset
- uspto-grants-1978_03
- Patent number
- US04077982
Reaction notes
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