Sodium hydride → HCID 20364891, compound

HRID 1679006Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][O:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][CH2:3]1.[H-].[Na+].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Cl>>[CH3:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][O:1][CH:2]1[CH2:3][O:4][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][CH2:7]1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 743621,3-Dioxan-5-ol, 2-phenyl-

HCID 814952-(Chloromethyl)anisole

Product 1

HCID 20364891HCID 20364891, compoundYield 77.9%

Conditions

Temperature: 100 °C

Procedure

5-Hydroxy-2-phenyl-1,3-dioxane (8.4 g, 0.05 mole) was reacted with sodium hydride and 2-methoxybenzyl chloride (7.8 g, 0.05 mol) according to the method of Example 2, except that the mixture was heated at 100° C for 12 hours, to give 11.7 g of yellow oil. The oil was distilled under 1 × 10-5 mm to give 4.6 g of product, which distilled at a pot temperature of 180°-190° C. VPC analysis of the product showed it to contain 72% cis-5-(2methoxybenzyloxy)-2-phenyl-1,3-dioxane.

Sources & evidence

ORD record: ord-25cedd1febbd46dda444e9faa737ecbd
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04077982

Reaction notes

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