p-Toluenesulfonic acid → HCID 20364950, compound

HRID 1679016Notes

Reaction equation

HRID 1679016 reaction equation
C(O[CH:4](OCC)[CH2:5][Cl:6])C.[F:10][C:11]1[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=1[CH2:13][O:14][C:15]([CH3:20])([CH2:18][OH:19])[CH2:16][OH:17].[C:25]1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:6][CH2:5][CH2:4][CH:25]1[O:19][CH2:18][C:15]([O:14][CH2:13][C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]=2[F:10])([CH3:20])[CH2:16][O:17]1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 121282-Chloro-1,1-diethoxyethaneHCID 20364943HCID 20364943, compound

Product 1

HCID 20364950HCID 20364950, compound

Procedure

According to the procedure of Example 47, 8.5 g of chloroacetaldehyde diethyl acetal and 11.0 g of 2-(2-fluorobenzyloxy)-2-methyl-1,3-propanediol were reacted in the presence of 0.02 g of p-toluenesulfonic acid to give, after separation by column chromatography, 5.1 g of t-2-(2-chloroethyl)-r-5-(2-fluorobenzyloxy)-5-methyl-1,3-dioxane, b.p. 130°/0.005 mm, nD25 1.5026; and 4.3 g of c-2-(2-chloroethyl)-r-5-(2-fluorobenzyloxy)-5-methyl-1,3-dioxane, b.p. 120°/0.01 mm; nD25 1.5050. The ir and nmr spectra were consistent with the assigned structures.

Workup

  1. customto give
  2. customafter separation by column chromatography, 5.1 g of t-2-(2-chloroethyl)-r-5-(2-fluorobenzyloxy)-5-methyl-1,3-dioxane, b.p. 130°/0.005 mm

Sources & evidence

ORD record
ord-6f7ed8d04c044120a62fb5ed01d2ba2b
Source dataset
uspto-grants-1978_03
Patent number
US04077982

Reaction notes

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