Benzoyl chloride → 4-Benzoyloxy-2,3-dimethoxy-5-methylphenol

HRID 277637Notes

Reaction equation

HRID 277637 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([OH:11])[C:6]([CH3:12])=[CH:5][C:4]=1[OH:13].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:14]([O:11][C:7]1[C:6]([CH3:12])=[CH:5][C:4]([OH:13])=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 111830272,3-Dimethoxy-5-methyl-1,4-benzenediol

Product 1

HCID 226253634-Benzoyloxy-2,3-dimethoxy-5-methylphenolYield 71.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using 5.05 g of 2,3-dimethoxy-5-methyl-1,4-dihydroxybenzene, 3.80 g of benzoyl chloride and 100 ml of pyridine, reaction and workup carried out as in the Reference Example gave 5.57 g of 4-benzoyloxy-2,3-dimethoxy-5-methylphenol, m.p. 109-111° C. Then, this 5.57 g was dissolved in 50 ml of DMF and added dropwise under an argon gas flow to a suspension of 0.84 g of sodium hydride in 50 ml of DMF. After the addition, stirring was continued for 30 minutes, and 2.6 ml of benzyl bromide was added dropwise and stirring continued for 2 hours at room temperature. The reaction mixture was poured into ice water, extracted with ethyl ether, washed with water, the solvent evaporated under reduced pressure, and thus obtained residue dissolved in 100 ml of methyl alcohol, and to this was added dropwise 5.10 g of sodium methylate (28% methyl alcohol solution) under ice-cooling and stirred for 12 hours at room temperature. Evaporation of the solvent under reduced pressure, neutralization with 2N HCl, extraction with ethyl ether and then evaporation of the solvent under reduced pressure gave 3.69 g of yellow oil.

Sources & evidence

ORD record
ord-24e7a32137144561ac0558a07e780ea7
Source dataset
uspto-grants-2002_03
Patent number
US06358515B2

Reaction notes

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