Dimethyl Sulfate → 2,2'-Dimethoxy-1,1'-binaphthalene

HRID 2425303Notes

Reaction equation

[OH-:1].[Na+].O[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1O.[CH2:25]([N+](CCCC)(CCCC)CCCC)CCC.S([O:47][CH3:48])(OC)(=O)=O>CC1C=CC=CC=1>[CH3:25][O:1][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[O:47][CH3:48]

Participants

Conditions

Temperature: 70 °C

Procedure

Prepare a 30% solution with 52 g NaOH at room temperature. Agitate 143 g 2,2′-dihydroxyl-1,1′-binaphthyl prepared as per the said method, 5.2 g tetrabutyl ammonium hydrosulfate and 500 ml methylbenzene, raise the temperature to 70° C. and add 164 g dimethyl sulfate dropwise simultaneously; agitate and react and conduct TLC track; when monoether point disappear, maintain the reaction for a period of time. Cool down and filter the solution; scrub the filter cake with 400 ml methylbenzene and 400 ml 5% NaOH solution successively and then scrub it with water to neutral state; dry it to obtain 2,2′-dimethoxy-1,1′-binaphthyl. The HPLC analysis results are as follows: the conversion of 2,2′-dihydroxyl-1,1′-binaphthyl ≧99%, the purity of 2,2′-dimethoxy-1,1′-binaphthyl ≧98% and the yield of 2,2′-dimethoxy-1,1′-binaphthyl ≧95%. Incorporate the methylbenzene layers and distill and recover the solid wastes. The distilled methylbenzene can be recycled.

Workup

stirringagitate
customreact
temperaturemaintain
customthe reaction for a period of time
temperatureCool down
filtrationfilter the solution
customdry it

Sources & evidence

ORD record: ord-df45d91eda914066ba2b3eb0b01967bf
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964678B2

Reaction notes

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