Methanesulfonic Acid → HCID 14751749, compound

HRID 1757077Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)([CH3:3])[CH3:2].[CH3:14][S:15]([OH:18])(=O)=[O:16].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[OH:10][C:7]1[CH:8]=[CH:9][C:14]([S:15]([C:5]2[C:6]([O:12][CH3:13])=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=2[CH:1]([CH3:3])[CH3:2])(=[O:18])=[O:16])=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 6395Methanesulfonic Acid

HCID 14812Phosphorus oxide (P4O10)

HCID 10910154HCID 10910154, compound

Product 1

HCID 14751749HCID 14751749, compound

Conditions

Temperature: 50 °C

Procedure

A mixture of 2 g (0.011 mole) of 1-isopropyl 3,4-dimethoxy benzene, 3.4 g (0.011 mole) of sodium 4-benzyloxy benzenesulfonate, 45 ml of anhydrous methanesulfonic acid and 4.5 g of phosphoric anhydride is stirred at 50° C. for 5 hours. It is poured into an ice/water mixture, the product is filtered off and washed on the filter with water. The still moist solid is taken up in 20 ml of ethanol and 5 ml of a 30% sodium hydroxide solution. It is heated at 60° C. for about 2 h until dissolution is complete, the solution is diluted with water, filtered and acidified with acetic acid. The product is filtered off and washed on the filter with water. It is then purified by chromatography on a column of silica using a dichloroethane/ethyl acetate mixture 95/5.

Workup

filtrationthe product is filtered off
washwashed on the
filtrationfilter with water
temperatureIt is heated at 60° C. for about 2 h until dissolution
additionthe solution is diluted with water
filtrationfiltered
filtrationThe product is filtered off
washwashed on the
filtrationfilter with water
customIt is then purified by chromatography on a column of silica using a dichloroethane/ethyl acetate mixture 95/5

Sources & evidence

ORD record: ord-6df053aacf4f40199a1ff146c17997cb
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05444056

Reaction notes

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