Piperonal → Bis(1,3-benzodioxol-5-yl)methanol

HRID 2378175Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.Br[C:13]1[CH:21]=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[CH:14]=1.C([Li])CCC.O1C2C=CC(C(C3C=C(OC)C=C(OC)C=3)O)=CC=2OCC1>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:13]3[CH:21]=[CH:20][C:16]4[O:17][CH2:18][O:19][C:15]=4[CH:14]=3)[OH:11])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Reactant 4

HCID 8438Piperonal

HCID 758311-Bromo-3,4-(methylenedioxy)benzene

HCID 69202534(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol

HCID 178418339Butyllithium

Product 1

HCID 384225Bis(1,3-benzodioxol-5-yl)methanolYield 83%

Procedure

Benzo[1,3]dioxole-5-carbaldehyde (1.80 g, 11.96 mmol), 5-bromobenzo[1,3]dioxole (2.65 g, 13.16 mmol), and n-butyl lithium (5.26 ml, 13.16 mmol) were treated in the same manner as described above for the synthesis of (2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol. The crude material was purified via flash column chromatography (5% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.) to give bis-benzo[1,3]dioxol-5-yl-methanol as a light brown oil (2.69 g, 83%): 1HNMR (CDCl3) 6.86-6.74 (m, 6H, Ar), 5.93 (s, 4H, 2CH2), 5.68 (d, J=3 Hz, 1H, CHOH), 2.16 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

Workup

customThe crude material was purified via flash column chromatography (5% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.)

Sources & evidence

ORD record: ord-8f26af6044ec424b865d6be56a481163
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470723B2

Reaction notes

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