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Triethylamine → Methanesulfonic Acid

HRID 1946
Notes
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Reaction equation

HRID 1946 reaction equation
[CH:1]1([C:7]2[C:8]([OH:37])=[CH:9][C:10]([CH3:36])=[C:11]([CH:13]([C:22]3[CH:27]=[C:26]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)[C:25]([OH:34])=[CH:24][C:23]=3[CH3:35])[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:21])[CH:15]=3)[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:38][S:39](Cl)(=[O:41])=[O:40].C(N(CC)CC)C>O1CCOCC1>[CH:28]1([C:26]2[C:25]([OH:34])=[CH:24][C:23]([CH3:35])=[C:22]([CH:13]([C:11]3[CH:12]=[C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[C:8]([OH:37])=[CH:9][C:10]=3[CH3:36])[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:21])[CH:15]=3)[CH:27]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[CH3:38][S:39]([OH:41])(=[O:20])=[O:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 157892294-[Bis(5-cyclohexyl-4-hydroxy-2-methylphenyl)methyl]benzene-1,2-diol

Product 2

HCID 6395Methanesulfonic AcidHCID 157892294-[Bis(5-cyclohexyl-4-hydroxy-2-methylphenyl)methyl]benzene-1,2-diol

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent
2×

Procedure

Bis(5 -cyclohexyl-4-hydroxy-2-methylphenyl)-3,4-dihydroxyphenylmethane(1.0 mole), 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 (1,500 g) having triethylamine (500 g) dissolved therein was added dropwise over 40 minutes at a controlled temperature not higher than 35° C. The precipitating salt was separated by filtration and the thus recovered reaction product was washed and dried to yield a mixed ester of bis(5-cyclohexyl-4-hydroxy-2-methylphenyl)-3,4-dihydroxyphenylmethane with naphthoquinone-1,2-diazido-5-sulfonic acid and methanesulfonic acid; the average degree of esterification was 50% for the quinonediazidosulfonate ester and 12% for the methanesulfonate ester.

Workup

  1. dissolutiondissolved
  2. additiontherein was added dropwise over 40 minutes at a controlled temperature not higher than 35° 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-1a28675e5d044056be5059476c8f3ce9
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728504

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes