Sulfuric Acid → (4S)-4-(2-tetrahydropyranyloxy)-2-nonynal

HRID 973339Notes

Reaction equation

HRID 973339 reaction equation
[OH:1][C@@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]#[C:4][CH:5]=[O:6].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.S(=O)(=O)(O)O>O.CCOCC>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:1][C@@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]#[C:4][CH:5]=[O:6]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 80803,4-dihydro-2H-pyranHCID 86735171(4S)-4-hydroxy-2-nonynal

Product 1

HCID 86735172(4S)-4-(2-tetrahydropyranyloxy)-2-nonynal

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of (4S)-4-hydroxy-2-nonynal (41.6 g., 0.27 mole) and dihydropyran (33.6 g., 0.4 mole) is cooled to 5° by means of an ice bath and is treated with 0.2 mole of concentrated sulfuric acid. This is allowed to warm to room temperature and stand 17 hours. It is then diluted with water. The oily product is taken up in ether, washed with sodium bicarbonate solution and water and dried over sodium sulfate. Distillation affords (4S)-4-(2-tetrahydropyranyloxy)-2-nonynal as a colorless oil.

Workup

  1. temperatureis cooled to 5° by means of an ice bath
  2. washwashed with sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. distillationDistillation

Sources & evidence

ORD record
ord-4b333c9749534a9cbe1332309c788255
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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