Hydrochloric Acid → Methyl 11-mercaptoundecanoate

HRID 653350Notes

Reaction equation

HRID 653350 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]CCC(OC)=O)(=[S:3])C.Cl.[C:19]([O:22][CH2:23]C)(=[O:21])[CH3:20].C(CC(C)(C)C)(C)C.C(=O)([O-])O.[Na+]>CO.ClCCl>[SH:3][CH2:1][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:20][C:19]([O:22][CH3:23])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 18516502EtOAc isooctaneHCID 20195807Methyl 11-thioacetylundecanoate

Product 1

HCID 406973Methyl 11-mercaptoundecanoateYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Compound 104 (15.6 g, 56.9 mmol) in methanol (50 ml) was added to a solution of hydrogen chloride in methanol (HCl was bubbled into 600 ml of MeOH for 10 min). The reaction was monitored by TLC (SiO2, ethyl acetate:isooctane 1:5). After 48 h, an excess of sodium hydrogen carbonate was added and the mixture was diluted with dichloromethane (150 ml), filtered and concentrated. Distillation gave pure 105 (9.0 g, 68%) with b.p. 93°-94° (7×10-2 torr). 1H-NMR (CDCl3, Me4Si) δ 3.68 (s, 3H, MeO), 2.53 (q, 2H, J~7 Hz, H--S--CH2), 2.31 (t, 2H, J=7.5 Hz, CH2CO). 13C-NMR (CDCl3, Me4Si) δ 174.2 (CO), 51.3, 34.0, 33.9, 29.3, 29.2, 29.1, 29.0, 28.9, 28.3, 24.8, 24.5.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. distillationDistillation

Sources & evidence

ORD record
ord-6f7b4dd365b04838b527d228d5f096d7
Source dataset
uspto-grants-1987_06
Patent number
US04675392

Reaction notes

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