Hydrochloric Acid → HCID 54566846, compound

HRID 986546Notes

Reaction equation

HRID 986546 reaction equation
[C:1]([C:14]1[CH:25]=[CH:24][C:17]([CH:18]=[CH:19][C:20]([O:22]C)=[O:21])=[CH:16][CH:15]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].O.[OH-].[Li+].Cl>O1CCCC1.O>[C:1]([C:14]1[CH:15]=[CH:16][C:17]([CH:18]=[CH:19][C:20]([OH:22])=[O:21])=[CH:24][CH:25]=1)#[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 53669740HCID 53669740, compound

Product 1

HCID 54566846HCID 54566846, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(1-tridecynyl)cinnamate (680 mg, 2 mmole) in tetrahydrofuran (25 ml) was added a solution of lithium hydroxide monohydrate (0.84 g) in water (25 ml) and the mixture was stirred overnight at room temperature. The cloudy mixture was acidified with dilute hydrochloric acid and then extracted with ether. The ethereal extracts were washed with brine, dried (MgSO4) and evaporated to a white crystalline solid. Yield 0.650 g (100%). Recrystallisation from methanol afforded material of mp 156°-157° C., υmax mull, 2650 (broad), 1710, 1685, 1630 cm-1, δ(DMSO), 0.85 (3H, distorted t, terminal CH3), 1.25 (18H, m, alkylene chain), ca 2.43 (2H, m, C≡C--CH2), 6.50 (1H, d, J 15.8 Hz, =CHCO2), 7.51 (4H, ABq, J 8.4 Hz, Δν22.4 Hz, arom), 7.57 (1 H, d, J 15.8 Hz, ArCH=), 12.5 (1H, broad, exchangeable, CO2H).

Workup

  1. extractionextracted with ether
  2. washThe ethereal extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to a white crystalline solid
  5. customRecrystallisation from methanol afforded material of mp 156°-157° C., υmax mull, 2650 (broad), 1710, 1685, 1630 cm-1, δ(DMSO), 0.85 (3H, distorted t, terminal CH3), 1.25 (18H, m, alkylene chain)

Sources & evidence

ORD record
ord-d1899ea9e92240489ef24b6310111d9a
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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