Hydrochloric Acid → HCID 60164157, compound

HRID 526821Notes

Reaction equation

HRID 526821 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:17]=[CH:16][C:7]2[C@H:8]([CH2:11][C:12]([O:14]C)=[O:13])[CH2:9][O:10][C:6]=2[CH:5]=1.Cl>CO>[OH:3][C:4]1[CH:17]=[CH:16][C:7]2[C@H:8]([CH2:11][C:12]([OH:14])=[O:13])[CH2:9][O:10][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53393313(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 60164157HCID 60164157, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 M aqueous sodium hydroxide solution (1081 mL) was added (internal temperature: 10 C or lower) to a solution of (S)-methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate (180 g) in methanol (360 mL) at 5 C over 30 minutes, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 1 M hydrochloric acid (2354 mL) was added at 5 C, followed by extraction with ethyl acetate (900 mL×2). The extracts were washed with brine (140 mL) and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (166 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate (900 mL×2)
  2. washThe extracts were washed with brine (140 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b0ecb97e6a714b8b8ee5b8fbdbd1e22b
Source dataset
uspto-grants-2016_05
Patent number
US09346776B2

Reaction notes

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