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(1S)-(+)-Camphor-10-sulphonic acid → 7-hydroxy-2,2-dimethyl-2H-chromene-3-carbaldehyde

HRID 217457
Notes
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Reaction equation

HRID 217457 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH:17]=[O:18])[C:11]([CH3:16])([CH3:15])[O:12]2)=[CH:7][CH:6]=1.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CCO>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH:17]=[O:18])[C:11]([CH3:15])([CH3:16])[O:12]2)=[CH:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 584386707-(methoxymethoxy)-2,2-dimethyl-2H-chromene-3-carbaldehyde

Product 1

HCID 584387357-hydroxy-2,2-dimethyl-2H-chromene-3-carbaldehydeYield 70.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

7-(Methoxymethoxy)-2,2-dimethyl-2H-chromene-3-carbaldehyde (300 mg) was dissolved in EtOH (10 mL), and (1S)-(+)-10-camphor sulfonic acid (421 mg) was added thereto, followed by stirring at 80° C. overnight. To the reaction liquid was added silica gel, followed by concentration. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=90:10 to 70:30) to obtain 7-hydroxy-2,2-dimethyl-2H-chromene-3-carbaldehyde (175 mg) as a red powder.

Workup

  1. customTo the reaction liquid
  2. additionwas added silica gel
  3. concentrationfollowed by concentration
  4. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=90:10 to 70:30)

Sources & evidence

ORD record
ord-5da2af6b21a34297b4ee7831ce2ed076
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193378B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes