Hydrochloric Acid → 2-(Benzo[b]thiophen-2-ylmethyl)malonic acid

HRID 926508Notes

Reaction equation

HRID 926508 reaction equation
[S:1]1[C:5]([CH2:6][CH:7]2[C:12](=[O:13])[O:11]C(C)(C)[O:9][C:8]2=[O:16])=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2.[OH-].[Na+].Cl>>[S:1]1[C:5]([CH2:6][CH:7]([C:12]([OH:13])=[O:11])[C:8]([OH:16])=[O:9])=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867155895-(Benzo[b]thiophen-2-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 867155902-(Benzo[b]thiophen-2-ylmethyl)malonic acid

Procedure

A solution of 5-(benzo[b]thiophen-2-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (2.0 g, 6.88 mmol, Intermediate 39: step a) and 3 M aqueous NaOH (14 mL) was heated in a 102° C. oil bath for 28 hours. The reaction mixture was poured over ice and acidified to pH 1 with concentrated aqueous HCl. The suspension was stirred at room temperature for 2 hours then filtered rinsing further with water and dried to provide the title compound as a tan solid.

Workup

  1. additionThe reaction mixture was poured over ice
  2. filtrationthen filtered
  3. washrinsing further with water
  4. customdried

Sources & evidence

ORD record
ord-4b57ce36f3c944c38da91b8860747c0a
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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