Hydrochloric Acid → HCID 22285080, compound

HRID 1061595Notes

Reaction equation

HRID 1061595 reaction equation
[OH-].[Na+].[C:3]([CH2:6][O:7][CH2:8][C:9]#[C:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][CH2:19][O:20][CH2:21][C:22]([O:24]C)=[O:23])=[CH:13][CH:12]=1)([OH:5])=[O:4].Cl>CO>[C:22]([CH2:21][O:20][CH2:19][C:18]#[C:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]#[C:9][CH2:8][O:7][CH2:6][C:3]([OH:5])=[O:4])=[CH:16][CH:15]=1)([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86759888HCID 86759888, compound

Product 1

HCID 22285080HCID 22285080, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous 2 N NaOH solution (10 ml) is added dropwise to a solution of methyl {3-[4-(3-carboxymethoxyprop-1-ynyl)phenyl]prop-2-ynyloxy)acetate (A31; 0.88 g, 2.7 mmol) in methanol (50 ml), and the mixture is stirred at RT for 2 h. The pH of the reaction solution is then adjusted to pH 2 using an aqueous 2 N HCl solution. The solution is extracted with ethyl acetate (30 ml, 2×) and washed with a saturated NaCl solution (30 ml). The combined organic phases are dried over MgSO4, filtered off and concentrated under reduced pressure. This gives the title compound (0.75 g) as a colorless powder.

Workup

  1. extractionThe solution is extracted with ethyl acetate (30 ml, 2×)
  2. washwashed with a saturated NaCl solution (30 ml)
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. filtrationfiltered off
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee68911f2a7147daa9aee54a69075cf2
Source dataset
uspto-grants-2005_11
Patent number
US06960588B1

Reaction notes

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