Acetyl chloride → 4-(Hydroxymethyl)-2-methoxyphenyl acetate

HRID 1798411Notes

Reaction equation

HRID 1798411 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:10][CH3:11].C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl>[C:19]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:10][CH3:11])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 62348Vanillyl alcohol

Product 1

HCID 111482684-(Hydroxymethyl)-2-methoxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A partial solution of 4-hydroxy-3-methoxybenzyl alcohol (1.23 g, 8 mmol), triethylamine (810 mg, 1.12 mL, 8 mmol) and 32 mL of dry CH2Cl2 was chilled in an ice bath. To the cold mixture was added dropwise acetyl chloride (628 mg, 570 μL, 8 mmol). The mixture was stirred at ice bath temperature 1 for one hour. Stirring at room temperature was allowed to take place overnight. The reaction mixture was diluted with CH2Cl2 and extracted with 1N HCl, water and saturated NaCl. The organic layer was dried over MgSO4, filtered and concentrated. Column chromatography on silica gel using CH2Cl2/MeOH (98:2, v/v) gave 548 mg (35%) of CO as a clear oil: Rf=0.22 (hexanes/ethyl acetate, 6:4 v/v); 1HNMR (CDCl3) δ 7.00 (d, 4J=1.5 Hz, 1H), 6.99 (d, 3J=8.5 Hz, 1H), 6.89 (dd, 3J=8.0 Hz, 4J=1.5 Hz, 1H), 5.27 (s, 2H), 4.66 (s, 2H), 3.83 (s, 3H) and 2.30 (s, 3H). Exact mass (FAB+) calculated for C10H12O4[M+] 196.0736. found 196.0739.

Workup

  1. stirringStirring at room temperature
  2. waitto take place overnight
  3. extractionextracted with 1N HCl, water and saturated NaCl
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customv/v) gave 548 mg (35%) of CO as a clear oil

Sources & evidence

ORD record
ord-3bc879707baf40ad82cc822678c186ea
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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