Piperonyl alcohol → HCID 66906062, compound

HRID 1915159Notes

Reaction equation

HRID 1915159 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[O:16]1[C:20]2[CH:21]=[CH:22][C:23]([CH2:25]O)=[CH:24][C:19]=2[O:18][CH2:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([O:14][CH2:25][C:23]2[CH:22]=[CH:21][C:20]3[O:16][CH2:17][O:18][C:19]=3[CH:24]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 10322Piperonyl alcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 12223651Dimethyl 3-hydroxyphthalate

Product 1

HCID 66906062HCID 66906062, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.0 g, 4.8 mmol), benzo[1,3]dioxol-5-yl-methanol (1.4 g, 9.5 mmol), and polymer-supported triphenyl phosphine (3.0 g, 9.5 mmol) in THF (30 mL) in an ice-bath was slowly added diisopropyl azodicarboxylate (1.9 mL, 9.5 mmol) and stirred at r.t. overnight. The mixture was filtered and the filter was washed with ethyl acetate (10 mL). The filtrate was evaporated and the residue was purified by flash column chromatography (EtOAc/Hexane) to give 3-(benzo[1,3]dioxol-5-ylmethoxy)-phthalic acid dimethyl ester (1.7 g, 102% crude yield). The product was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter was washed with ethyl acetate (10 mL)
  3. customThe filtrate was evaporated
  4. customthe residue was purified by flash column chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-2975b2f17bb4453c8b31aea23d471f21
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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