HCID 20139219, compound → HCID 14207573, compound

HRID 1252722Notes

Reaction equation

HRID 1252722 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:20]([O:22]C)=[O:21])[C:12](=[C:17]([CH3:19])[CH:18]=1)[C:13]([O:15][CH3:16])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[Na+].COCCOC>[C:13]([C:12]1[C:17]([CH3:19])=[CH:18][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]=1[C:20]([OH:22])=[O:21])([O:15][CH3:16])=[O:14]

Participants

4

Reactant 1

HCID 20139219HCID 20139219, compound

Product 1

HCID 14207573HCID 14207573, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of dimethyl 4-benzyloxy-6-methyl-phthalate (1.5 gm) in sodium hydroxide (2% solution, 12 ml) and 1,2-dimethoxyethane (12 ml) was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure. The aqueous solution was washed with ethyl acetate (3×125 ml). The organic extract was dried over magnesium sulphate and evaporated to give a solid. This solid was recrystallized from ethyl acetate: pet. ether 30-60 to yield 2-carbomethoxy-3-methyl-5-benzyloxy-benzoic acid (750 mg), m.p. 132°-133° C., IR (KBr): 2500-3200, 1725, 1685, 1600 cm-1. Anal. calcd. for C17H16O5 : C, 67.99, H, 5.37. Found: C, 68.01, H, 5.42.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washThe aqueous solution was washed with ethyl acetate (3×125 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulphate
  5. customevaporated
  6. customto give a solid
  7. customThis solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1bb8d923187e40f7bbca155241e64df6
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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