Methanol → 5-(4H-1,3-Benzodioxin-2-yl)-2-methoxyphenol

HRID 614880Notes

Reaction equation

HRID 614880 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]C1.[CH3:11][OH:12].[CH3:13][O-:14].[Ba+2].C[O-]>C1C=CC=CC=1>[OH:1][C:6]1[CH:7]=[C:8]([CH:11]2[O:14][C:13]3[CH:9]=[CH:10][CH:5]=[CH:6][C:7]=3[CH2:8][O:12]2)[CH:9]=[CH:10][C:5]=1[O:4][CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 103011,4-BenzodioxanHCID 13438163Barium methanolate

Product 1

HCID 5923775-(4H-1,3-Benzodioxin-2-yl)-2-methoxyphenol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 30-g. portion of the benzodioxan compound prepared in Example 1C was dissolved in 300 ml. of warm benzene, diluted with 600 ml. of methanol containing 70 mmol. of barium methoxide, and then stored 18 hours at 5° C. After adding 10 g. of ammonium acetate, volatiles were evaporated and the residue was extracted with two 500-ml. portions of chloroform. The chloroform was washed once with 500 ml. of water, the water was reextracted with 500 ml. of chloroform, and the combined chloroform extracts were washed once with 300 ml. of water. Evaporation and crystallization from diethyl ether-n-hexane gave the neutral form of the novel sweet compound (23 g., 95%), m.p. 105°-106° C.

Workup

  1. additionAfter adding 10 g
  2. customof ammonium acetate, volatiles were evaporated
  3. extractionthe residue was extracted with two 500-ml
  4. washThe chloroform was washed once with 500 ml
  5. washof chloroform, and the combined chloroform extracts were washed once with 300 ml
  6. customEvaporation and crystallization from diethyl ether-n-hexane
  7. customgave the neutral form of the novel sweet compound (23 g., 95%), m.p. 105°-106° C.

Sources & evidence

ORD record
ord-91f1bbd1e9284077a666d6c9a495aaed
Source dataset
uspto-grants-1979_03
Patent number
US04146650

Reaction notes

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