Hydrochloric Acid → HCID 19606346, compound

HRID 1603898Notes

Reaction equation

HRID 1603898 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([C:19]([O:21]CC)=[O:20])[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl>CO>[CH2:1]([O:8][CH2:9][C:10]1([C:19]([OH:21])=[O:20])[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 19606265HCID 19606265, compound

Product 1

HCID 19606346HCID 19606346, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of ethyl 2-benzyloxymethyl-2,3-dihydrobenzofuran-2-carboxylate (1.62 g, 5.47 mmol) in methanol (70 ml) was added with a solution of 1M lithium hydroxide (54.7 ml). The mixture was refluxed under stirring for 3 h, after that was neutralized with 1M HCl and methanol was evaporated off under reduced pressure. The resulting crude was suspended in water (20 ml) and extracted with ethyl acetate (4×25 ml). The organic phase was dried and the solvent was evaporated off under reduced pressure, to obtain 1.436 g of the title compound, which was purified by crystallization in methanol (97% yield).

Workup

  1. temperatureThe mixture was refluxed
  2. customwas evaporated off under reduced pressure
  3. extractionextracted with ethyl acetate (4×25 ml)
  4. customThe organic phase was dried
  5. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-a85d553b614648e4a058cf01210238b2
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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