Sodium Hydroxide → (E)-6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid

HRID 1781524Notes

Reaction equation

HRID 1781524 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[C:4]=1[CH2:21]/[CH:22]=[C:23](\[CH3:30])/[CH2:24][CH2:25][C:26]([O:28]C)=[O:27].[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[C:4]=1[CH2:21]/[CH:22]=[C:23](\[CH3:30])/[CH2:24][CH2:25][C:26]([OH:28])=[O:27]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10342183(E)-6-[1,3-Dihydro-6-methoxy-4-[(2-methoxyethoxy)methoxy]-7-methyl-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoic Acid Methyl Ester

Product 1

HCID 10250873(E)-6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To methyl (E)-6-(1,3-dihydro-6-methoxy -4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (76.0 g) in methanol (300 ml) was added 1N aqueous sodium hydroxide (300 ml). After 11/2 hours the solution was diluted with water, washed twice with ether, then acidified with dilute hydrochloric acid. The acidified solution was extracted with ether, and the extract was dried and evaporated to give (E)-6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy -7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid, m.p. 77°-82° C. (etherhexane).

Workup

  1. washwashed twice with ether
  2. extractionThe acidified solution was extracted with ether
  3. customthe extract was dried
  4. customevaporated

Sources & evidence

ORD record
ord-ea17c53062cd4009bf12f9a094220e13
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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