Acetic Acid → HCID 66750527, compound

HRID 643902Notes

Reaction equation

HRID 643902 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([OH:13])[CH2:10]2)=[CH:5][CH:4]=1.[CH3:14][C:15](O)=[O:16]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([O:13][C:15](=[O:16])[CH3:14])[CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 230252467-Methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

Product 1

HCID 66750527HCID 66750527, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
0 °C

Procedure

7-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ol (4.48 g, from step A) is taken up in AcOH (15 mL) and cooled to 0° C. Concentrated sulfuric acid (10 drops) is added. The mixture is stirred at 0° C. for 20 min and then warmed to room temperature over 10 min. The mixture is partitioned between ice-cold 1 N NaOH and EtOAc. The organic layer is dried over MgSO4 and concentrated to afford acetic acid 7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl ester as a red solid: 1H NMR (CDCl3) δ 7.01 (d, J=8.0 Hz, 1H), 6.71 (d, J=8.0 Hz, 1H), 6.60 (s, 1H), 5.19 (m, 1H), 3.77 (s, 3H), 3.08 (dd, J=16.0, 8.0 Hz, 1H), 2.90-2.70 (m, 3H), 2.05 (s, 3H), 2.05-1.88 (m, 2H).

Workup

  1. temperaturewarmed to room temperature over 10 min
  2. customThe mixture is partitioned between ice-cold 1 N NaOH and EtOAc
  3. dry with materialThe organic layer is dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-09180a015d8743ca92a99b5af8c5b9c7
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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