Acetic Acid → 6-(2-Tetrahydropyranyloxy)hexanal

HRID 1581107Notes

Reaction equation

HRID 1581107 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].C(N(CC)CC)C.C(O)(=O)C.O>CS(C)=O.C(OCC)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8471TriethylamineHCID 5589936-(Tetrahydro-2H-pyran-2-yloxy)-1-hexanol

Product 1

HCID 108673416-(2-Tetrahydropyranyloxy)hexanalYield 64.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Pyridine-sulphur trioxide complex (17.1 g., 0.108 mole) in dimethylsulphoxide (90 ml.) was added dropwise to a mixture of 6-(2-tetrahydropyranyloxy)-hexanol (7.2 g., 0.036 mole) and triethylamine (27 g., 0.27 mole) in dimethylsulphoxide (90 ml.) at 25°C. The mixture was stirred for a further hour, then 2N acetic acid (100 ml.), water (200 ml.) and diethyl ether (500 ml.) added successively, the layers separated and the aqueous layer extracted with diethyl ether. The combined ether solutions were washed quickly with 2N hydrochloric acid, aqueous sodium carbonate and then water, and dried over sodium sulphate. The solvent was evaporated and the residue distilled under reduced pressure to give 6-(2-tetrahydropyranyloxy)hexanal (4.65 g., 63%), b.p. 75°-105°C./0.15 mm.Hg.

Workup

  1. customthe layers separated
  2. extractionthe aqueous layer extracted with diethyl ether
  3. washThe combined ether solutions were washed quickly with 2N hydrochloric acid, aqueous sodium carbonate
  4. dry with materialwater, and dried over sodium sulphate
  5. customThe solvent was evaporated
  6. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-7dcf48507b3b45e296cd447f1d07488f
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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