Hydrochloric Acid → 1-Formyl-4-(3-hydroxypropyl)naphthalene

HRID 1166746Notes

Reaction equation

HRID 1166746 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2OCC[O:16]2)=[CH:7][CH:6]=1.Cl>C1COCC1.C(OCC)C>[CH:15]([C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([CH2:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=1)=[O:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 538626532-[4-(3-Hydroxypropyl)naphthyl]dioxolane

Product 1

HCID 229990881-Formyl-4-(3-hydroxypropyl)naphthaleneYield 72%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(3-hydroxypropyl)naphthyl]dioxolane (67 mg, 0.26 mmol) in anhydrous THF (5 mL) was added 1 N hydrochloric acid (1 mL). The mixture was stirred at room temperature for 48 hr, diluted with ethyl ether (20 mL), washed with satd. NaHCO3 solution (2×10 mL), dried (MgSO4), concentrated and coevaporated with CHCl3 (3×10 mL) to yield 40 mg (72%) of a colorless oil.

Workup

  1. washwashed with satd
  2. dry with materialNaHCO3 solution (2×10 mL), dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-75ee93236f24446fba7e33b0951922d5
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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