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 2396650Notes

Reaction equation

HRID 2396650 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-db357d8bb11f4485a2ebb5572d1e5f09
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

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