Acetyl chloride → 4-Acetyl-2,6-dimethoxyphenyl acetate

HRID 2065980Notes

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([OH:12])=[C:6]([O:13][CH3:14])[CH:5]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29]>ClCCl.O>[C:28]([O:12][C:7]1[C:6]([O:13][CH3:14])=[CH:5][C:4]([C:2](=[O:3])[CH3:1])=[CH:9][C:8]=1[O:10][CH3:11])(=[O:30])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

3.0 g (15.3 mmol) of 3,5-dimethoxy-4-hydroxyacetophenone is dissolved in dichloromethane (30 ml) and 2.53 g (18.3 mmol) of K2CO3 is added. Triethylamine (2.6 ml) is then added dropwise. The reaction medium is cooled down to 0° C. and acetyl chloride (1.31 ml; 18.3 mmol) is added. The mixture is stirred for 24 hours at ambient temperature then poured into ice-cooled water. After extraction with dichloromethane, the organic phase is washed with sodium chloride in a saturated aqueous solution before being dried over magnesium sulphate, filtered and concentrated under vacuum. The product obtained is purified by crystallization from ether in order to produce a white solid with a yield of 99%. Melting point: 145° C.

Workup

additionthen poured into ice-
extractionAfter extraction with dichloromethane
washthe organic phase is washed with sodium chloride in a saturated aqueous solution
dry with materialbefore being dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under vacuum
customThe product obtained
customis purified by crystallization from ether in order
customto produce a white solid with a yield of 99%

Sources & evidence

ORD record: ord-b02e5eb6154b492cb64c673d9c4fe1b7
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288560B2

Reaction notes

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