Triethylamine → 2-Formyl-5-methoxy-6-methyl-3-[dimethyl-(1,1,2-trimethyl-propyl)silanyloxy]-benzoic acid allyl ester

HRID 1377843Notes

Reaction equation

HRID 1377843 reaction equation
[CH2:1]([O:4][C:5](=[O:18])[C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[CH:9]=[C:8]([OH:15])[C:7]=1[CH:16]=[O:17])[CH:2]=[CH2:3].[CH3:19][Si:20]([CH3:28])([C:22]([CH3:27])([CH3:26])[CH:23]([CH3:25])[CH3:24])Cl.C(N(CC)CC)C>CN(C)C=O>[CH2:1]([O:4][C:5](=[O:18])[C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[CH:9]=[C:8]([O:15][Si:20]([CH3:28])([CH3:19])[C:22]([CH3:27])([CH3:26])[CH:23]([CH3:25])[CH3:24])[C:7]=1[CH:16]=[O:17])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 144239Dimethylthexylsilyl chlorideHCID 537352632-Formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid allyl ester

Product 1

HCID 537110522-Formyl-5-methoxy-6-methyl-3-[dimethyl-(1,1,2-trimethyl-propyl)silanyloxy]-benzoic acid allyl esterYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 75.1 g of 2-formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid allyl ester in 0.6 l of N,N-dimethylformamide were added 81.0 g of dimethyl-(1,1,2-trimethyl-propyl)-chlorosilane and 45.5 g of triethylamine. The mixture was stirred for 4 h at room temperature and then evaporated in vacuo. The residue was taken up in 2 l of ethyl acetate, and the mixture was successively washed with 1N hydrochloric acid and with brine, and dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was crystallized from hexane to give 108.8 g of 2-formyl-5-methoxy-6-methyl-3-[dimethyl-(1,1,2-trimethyl-propyl)silanyloxy]-benzoic acid allyl ester as white crystals of m.p. 81°-82° C.

Workup

  1. customevaporated in vacuo
  2. washthe mixture was successively washed with 1N hydrochloric acid and with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-e5a55fffd8b1453484ccedea206df02e
Source dataset
uspto-grants-1997_09
Patent number
US05665746

Reaction notes

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