Hydrochloric Acid → HCID 83484100, compound

HRID 931094Notes

Reaction equation

HRID 931094 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.Cl.O.[CH2:16]([C:23]1([CH2:27][OH:28])[CH2:26][O:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O.[O-2].[Cr+6].[O-2].[O-2].C(O)(C)C>[CH2:16]([C:23]1([C:27]([OH:3])=[O:28])[CH2:24][O:25][CH2:26]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 20063132HCID 20063132, compoundHCID 131709961Jones' reagent

Product 1

HCID 83484100HCID 83484100, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

Jones reagent, (130 mL of a 2.3 M solution) previously prepared by adding hydrochloric acid (46 mL) to water (150 mL) followed by chromium (VI) oxide (55.5 g), was added dropwise to a solution of (3-benzyloxetan-3-yl)methanol (40 g, 0.2 mol) in acetone (600 mL). The reaction mixture was stirred at room temperature for 5 h. Isopropanol (18 g) was added and the mixture was extracted with ether (4 L), washed with NaH2PO4 (1M in water, 200 mL) and sodium chloride (1 M in water, 200 mL). The organics were dried over sodium sulfate, filtered and concentrated. The residue was triturated with ether (100 mL) to afford the title compound (37 g, 0.2 mol, 85%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 3.22 (s, 2H), 4.49-4.51 (d, 2H), 4.65-4.67 (d, 2H), 7.12-7.27 (m, 5H), 12.85 (s, 1H).

Workup

  1. extractionthe mixture was extracted with ether (4 L)
  2. washwashed with NaH2PO4 (1M in water, 200 mL) and sodium chloride (1 M in water, 200 mL)
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was triturated with ether (100 mL)

Sources & evidence

ORD record
ord-a4e551b58295409c992883f6919b61e7
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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