Phosphoric Acid → 2,2-Diphenyl-1,3-benzodioxol-5-carbaldehyde

HRID 1755886Notes

Reaction equation

Br[C:2]1[CH:22]=[CH:21][C:5]2[O:6][C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.C([Li])CCC.CN(C)[CH:30]=[O:31].P(=O)(O)(O)O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[C:9]1([C:7]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:6][C:5]3[CH:21]=[CH:22][C:2]([CH:30]=[O:31])=[CH:3][C:4]=3[O:8]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -10 °C

Procedure

5-Bromo-2,2-diphenyl-1,3-benzodioxol (70 g) in 440 ml of tetrahydrofuran are treated at -78° C. with 125 ml of a 1.6M solution of butyllithium in n-hexane. After 10 minutes 40 ml of dimethylformamide are added thereto and the mixture is left to warm to -10° C. Thereafter, 70 ml of 20% aqueous phosphoric acid and 500 ml of ethyl acetate are added, the organic phase is separated and evaporated. The residue is recrystallized from 130 ml of ethanol. 49.5 g of 2,2-diphenyl-1,3-benzodioxol-5-carbaldehyde are obtained.

Workup

waitthe mixture is left
customthe organic phase is separated
customevaporated
customThe residue is recrystallized from 130 ml of ethanol

Sources & evidence

ORD record: ord-dd0c9a7d67a64953b1bf4b26a36ea86e
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438052

Reaction notes

Loading…