p-Toluenesulfonic acid → 4,5-Dihydro-2-methoxy-5,5-dimethyl-1,3-benzodioxepin-7-yl methanesulphonate

HRID 27637Notes

Reaction equation

[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[CH:7]=1)(=[O:4])=[O:3].[CH:18](OC)(OC)[O:19][CH3:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH:18]([O:19][CH3:20])[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:8]=2[CH:7]=1)(=[O:4])=[O:3]

Participants

Reactant 3

HCID 6101p-Toluenesulfonic acid

HCID 9005Trimethyl orthoformate

HCID 233412804-Hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl methanesulphonate

Product 1

HCID 233412864,5-Dihydro-2-methoxy-5,5-dimethyl-1,3-benzodioxepin-7-yl methanesulphonateYield 79%

Procedure

4-Hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl methanesulphonate (10.4 parts) (from Example 1) was reacted with trimethyl orthoformate (127 parts) in the presence of p-toluenesulphonic acid (0.05 parts) as in Example 20 to produce 4,5-dihydro-2-methoxy-5,5-dimethyl-1,3-benzodioxepin-7-yl methanesulphonate (9.5 parts, 79% yield) as a colourless oil.

Sources & evidence

ORD record: ord-4ec8331f07f24efea69e55480a413dce
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04222767

Reaction notes

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