HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sulfuric Acid → 4-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione

HRID 879085
Notes
Print preview

Reaction equation

HRID 879085 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[C:16]([CH:22]2[C:24]3([C:28](=[O:29])[C:27]([CH3:31])([CH3:30])[O:26][C:25]3([CH3:33])[CH3:32])[O:23]2)[CH:15]=1>ClCCCl>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[C:16]([CH:22]2[C:28](=[O:29])[C:27]([CH3:31])([CH3:30])[O:26][C:25]([CH3:33])([CH3:32])[C:24]2=[O:23])[CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 866636752-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one

Product 1

HCID 668235414-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cold solution of concentrated sulphuric acid (6 ml) is added a second solution of 2-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one (1.90 g, 0.0045 mol) in 1,2-dichloroethane (6 ml) dropwise over 5 mins. This biphasic mixture is stirred vigorously for 2 hours at 0° C., then is poured into ice and extracted with diethyl ether. All organics are combined, washed with brine, dried over magnesium sulfate then concentrated in vacuo. The crude product is purified by flash column chromatography (5% ethyl acetate in isohexane to 25% ethyl acetate in isohexane) to afford 4-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione as a yellow gum.

Workup

  1. additionis poured into ice
  2. extractionextracted with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationthen concentrated in vacuo
  6. customThe crude product is purified by flash column chromatography (5% ethyl acetate in isohexane to 25% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-7db0236c5aaf45c09753ce53275fc23e
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987476B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes