Sulfuric Acid → HCID 18434036, compound

HRID 2306010Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=O.C1(C)C=CC=CC=1.[CH3:22][O:23][C:24]1[CH:25]=C(O)[CH:27]=[CH:28][CH:29]=1.S(=O)(=O)(O)O>CO>[OH:1][C:2]1[CH:3]=[C:4]([C:5]2[C:27]3[C:11](=[CH:25][C:24]([O:23][CH3:22])=[CH:29][CH:28]=3)[O:10][C:8](=[O:9])[CH:7]=2)[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 25 °C

Procedure

The solution of methyl 3-hydroxybenzoylacetate (about 4.0 kg) and toluene (total weight of solution 5.6 kg) from the step above was charged to a reaction vessel along with 3-methoxyphenol (2.55 kg). The mixture was stirred vigorously at 0° C. while 27 M sulfuric acid (5.55 L) was added over 5 minutes. The resulting dark solution was warmed to 25° C. When the reaction began to thicken (40 minutes), methanol (21.8 L) was added. The addition was exothermic. Continued stirring (15 minutes) yielded a smooth, brown slurry which was cooled to 5° C. over 25 minutes, stirred for one hour, then filtered. The filter cake was washed with methanol (5.50 L) and dried under vacuum at 45-50° C. to give 3.70 kg (13.8 mol, 70% yield for two steps) of 4-[3′-(hydroxy)phenyl]-7-methoxycoumarin (a compound of Formula (b)).

Workup

additionwas added over 5 minutes
additionwas added
additionThe addition
customyielded a smooth, brown slurry which
temperaturewas cooled to 5° C. over 25 minutes
stirringstirred for one hour
filtrationfiltered
washThe filter cake was washed with methanol (5.50 L)
customdried under vacuum at 45-50° C.

Sources & evidence

ORD record: ord-022507020d8f4ddf884f2bd196dd7b0e
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441173B1

Reaction notes

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