Triethylamine → Methanesulfonic Acid

HRID 1947

Reaction equation

HRID 1947 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[CH3:18])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C>O1CCOCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[CH3:18])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:33][S:34]([OH:36])(=[O:1])=[O:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6342784,4'-(1-(4-(1-(4-Hydroxyphenyl)-1-methylethyl)phenyl)ethylidene)diphenol

Product 2

HCID 6395Methanesulfonic AcidHCID 6342784,4'-(1-(4-(1-(4-Hydroxyphenyl)-1-methylethyl)phenyl)ethylidene)diphenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

One (1.0) mole of 1-[1-(4-hydroxyphenyl)isopropyl]-4-[1,1-bis(4-hydroxyphenyl)ethyl]benzene, naphthoquinone-1,2-diazido-5-sulfonyl chloride (2.0 moles) and methanesulfonyl chloride (0.5 moles) were dissolved in dioxane (4,000 g). To the resulting solution, dioxane (2,000 g) having triethylamine (500 g) dissolved therein was added dropwise over 10 minutes at a controlled temperature not higher than 30° C. The precipitating salt was separated by filtration and the thus recovered reaction product was washed and dried to yield esters of the 1-[1-(4-hydroxyphenyl)isopropyl]-4-[1,1-bis(4-hydroxyphenyl)ethyl]benzene with naphthoquinone-1,2-diazido-5-sulfonic acid and methanesulfonic acid.

Workup

  1. dissolutiondissolved
  2. additiontherein was added dropwise over 10 minutes at a controlled temperature not higher than 30° C
  3. customThe precipitating salt was separated by filtration
  4. customthe thus recovered reaction product
  5. washwas washed
  6. customdried

Sources & evidence

ORD record
ord-cf4091059f4c4259bc4581b2905f26f6
Source dataset
uspto-grants-1998_03
Patent number
US05728504

Linked notes

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