Hydrochloric Acid → (E)-2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoic acid

HRID 1781564Notes

Reaction equation

HRID 1781564 reaction equation
[C:1]([O:4][C:5]1[C:13]([CH2:14]/[CH:15]=[CH:16]/[C:17]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=[O:20])=[C:12]([O:28][CH3:29])[C:11]([CH3:30])=[C:10]2[C:6]=1[C:7](=[O:31])[O:8][CH2:9]2)(=[O:3])[CH3:2].[OH-].[Li+].Cl>CO.O>[C:1]([O:4][C:5]1[C:13]([CH2:14]/[CH:15]=[CH:16]/[C:17]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([OH:21])=[O:20])=[C:12]([O:28][CH3:29])[C:11]([CH3:30])=[C:10]2[C:6]=1[C:7](=[O:31])[O:8][CH2:9]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86749277methyl (E) 2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate

Product 1

HCID 19046326(E)-2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of methyl (E)-2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate (0.1 g) and lithium hydroxide (0.06 g) in methanol (1 ml) and water (1 ml) was heated at 70° C. for 48 hours. The solution was cooled and poured into water, then acidified with 2N hydrochloric acid and extracted with ethyl acetate. The extract was dried and evaporated to give (E)-2-[3-(4-acetoxy-1,3-dihydro -6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop -1-en-1-yl ]-3-methylbenzoic acid, mp 180°-3° C. (ethyl acetate/cyclohexane).

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with ethyl acetate
  3. customThe extract was dried
  4. customevaporated

Sources & evidence

ORD record
ord-47c6f01829024b97bbd90d3a8cd2c7d7
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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