Sodium Sulfite → 4-p-Methoxybenzyloxycarbonyl-4-methylvaleric acid

HRID 1252218Notes

Reaction equation

HRID 1252218 reaction equation
S([O-])([O-])=O.[Na+].[Na+].[CH3:7][O:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][O:14][C:15]([C:17]([CH3:34])([CH3:33])[CH2:18][CH2:19][C:20]([O:22]CC2C=CC([N+]([O-])=O)=CC=2)=[O:21])=[O:16])=[CH:11][CH:10]=1>O.O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14][C:15]([C:17]([CH3:33])([CH3:34])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:16])=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 24437Sodium SulfiteHCID 20140840p-Nitrobenzyl 4-p-methoxybenzyloxycarbonyl-4-methylvalerate

Product 1

HCID 141557204-p-Methoxybenzyloxycarbonyl-4-methylvaleric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium sulfite hydrade (12.35 g) in water (70 ml) was added a solution of p-nitrobenzyl 4-p-methoxybenzyloxycarbonyl-4-methylvalerate (25.4 g) in tetrahydrofuran (140 ml). The reaction mixture was stirred at room temperature for 7.5 hours, diluted with water and washed with diethyl ether. The aqueous layer was acidified with hydrochloric acid and extracted with diethyl ether. The extract was washed with water, dried over anhydrous sodium sulfate and evaporated to give 4-p-methoxybenzyloxycarbonyl-4-methylvaleric acid.

Workup

  1. washwashed with diethyl ether
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-78dd7377fb6a46e2813f08950e124011
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

Loading…