Dimethyl Sulfoxide → HCID 14742766, compound

HRID 1651237Notes

Reaction equation

HRID 1651237 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([C:15]1[C:24]2[C:19](=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[CH2:27][OH:28])[CH2:12][CH2:13][CH3:14].C(N(CC)CC)C>ClCCl>[CH2:11]([C:15]1[C:24]2[C:19](=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[CH:27]=[O:28])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14742764HCID 14742764, compound

Product 1

HCID 14742766HCID 14742766, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of dimethylsulfoxide (0.54 mL) in dry dichloromethane (3 mL) was added with stirring to a chilled (<-60° C.) solution of oxalyl chloride (0.59 mL) in dry dichloromethane (15 mL) at such a rate that the reaction temperature did not exceed -60° C. After 15 minutes a solution of 1-butyl-5-methoxy-2-naphthalenemethanol (1.54 g) in dichloromethane (6 mL) was added while the reaction temperature was still maintained below -60° C. The reaction was allowed to proceed for 15 minutes then triethylamine (2.9 mL) was added to the chilled reaction and, after an additional 20 minutes the cooling bath was removed and the mixture was allowed to equilibrate to room temperature. After 2N hydrochloric acid (225 mL) was added, the layers were separated and the aqueous phase was extracted with dichloromethane (50 mL), then the combined organic extracts were dried (MgSO4) and evaporated to yield 1.6 g of 1-butyl-5 -methoxy-2-naphthalenecarboxaldehyde. Sublimation of a portion (50° C.; 0.1 mm) furnished the analytical sample, mp 61.5°-62.5° C. Anal. Calcd for C16H18O2 : C, 79.31; H, 7.49 Found: C, 79.02; H, 7.53

Workup

  1. customdid not exceed -60° C
  2. customwas still maintained below -60° C
  3. customwas removed
  4. customto equilibrate to room temperature
  5. additionAfter 2N hydrochloric acid (225 mL) was added
  6. customthe layers were separated
  7. extractionthe aqueous phase was extracted with dichloromethane (50 mL)
  8. dry with materialthe combined organic extracts were dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-f109a49fe0f94376ac7ffaec3bf3cd27
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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