Methanol → HCID 20059823, compound

HRID 232384Notes

Reaction equation

HRID 232384 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][C:17]([O:19]CC2C=CC=CC=2)=[O:18])=[C:11]([CH3:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+]>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:27])[C:12]([CH2:16][C:17]([OH:19])=[O:18])=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 20059716HCID 20059716, compound

Product 1

HCID 20059823HCID 20059823, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.35 g of benzyl 2-(4-benzyloxy-2,6-dimethylphenyl)acetate was shaken overnight with a mixture of 7 ml of methanol, 0.7 ml of water and 0.28 g of solid sodium hydroxide. The resulting solution was evaporated and the residue was partitioned between 50 ml of methylene chloride and 25 ml of 2M hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate and evaporated. The solid residue was recrystallized from a mixture of 3 ml of methanol and 3 ml of water to give 0.21 g of 2-(4-benzyloxy-2,6-dimethylphenyl)acetic acid of melting point 149°-150° C.

Workup

  1. customThe resulting solution was evaporated
  2. customthe residue was partitioned between 50 ml of methylene chloride and 25 ml of 2M hydrochloric acid
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe solid residue was recrystallized from a mixture of 3 ml of methanol and 3 ml of water

Sources & evidence

ORD record
ord-d835f946c7644b60a06fd60219d6c004
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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