Hydrochloric Acid → 3-(Tridec-1-ynyl)benzyl alcohol

HRID 255997

Reaction equation

HRID 255997 reaction equation
[C:1]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].CC(C[AlH]CC(C)C)C.Cl>C1COCC1>[C:1]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][OH:18])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 136885053-(1-Tridecynyl)benzaldehyde

Product 1

HCID 136885073-(Tridec-1-ynyl)benzyl alcoholYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(Tridec-1-ynyl)benzaldehyde (5.68 g, 20 mmol, from example 5) in THF (70 ml) at -78° C. was added DIBAL (22 ml, 1.1 eq, 1 molar solution in hexane). After warming slowly to room temperature the solution was stirred for 2 hr and then added to dilute hydrochloric acid (50 ml). The product was then extracted into diethyl ether (2×100 ml) and after washing with brine and drying (MgSO4) the ether was removed under reduced pressure. Distillation of the resulting oil yielded the desired product, (4.55 g, 79.5%), B.p. 210° C. at 0.1 mm Hg, νmax 690, 785, 1030, 1460, 1600, 2200, 2850, 2915 and 3300 cm-1 ; δ(CDCl3) 0.92 (3H, distorted t, terminal CH3), 1.3 (18H, m, alkylene chain), 1.9 (1H, s, hydroxyl), 2.35 (2H, t J= 7 Hz, CH2 adjacent to acetylene), 4.6 (2H, s, benzylics), 7.3 (4H, m, aromatics). M+ 286.2301, (C20H30O requires 286.2297).

Workup

  1. extractionThe product was then extracted into diethyl ether (2×100 ml)
  2. washafter washing with brine
  3. dry with materialdrying (MgSO4) the ether
  4. customwas removed under reduced pressure
  5. distillationDistillation of the resulting oil

Sources & evidence

ORD record
ord-fb051c5942d843faa439ebc99e09260c
Source dataset
uspto-grants-1987_10
Patent number
US04699995

Linked notes

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